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Facile Net Cycloaddition Approach to Optically Active 1,5-Benzothiazepines
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    Facile Net Cycloaddition Approach to Optically Active 1,5-Benzothiazepines
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    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2015, 137, 16, 5320–5323
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    https://doi.org/10.1021/jacs.5b02537
    Published April 9, 2015
    Copyright © 2015 American Chemical Society

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    The 1,5-benzothiazepine moiety is well-known as a versatile pharmacophore, and its derivatives are expected to have antagonism against numerous diseases. Thus, it is desirable to develop a synthetic route that enables facile enantioselective preparation of a wide range of such derivatives. Although the cycloaddition approach could be considered a possible route to these compounds, to date, there has been no precedent of such a protocol. We therefore present the first example of a highly enantioselective net [4 + 3] cycloaddition to afford 1,5-benzothiazepines by utilizing α,β-unsaturated acylammonium intermediates generated by chiral isothiourea catalysts, which undergo two sequential chemoselective nucleophilic attacks by 2-aminothiophenols. This protocol provided cycloadducts in extremely high regioselectivity, with a good-to-excellent stereoselectivity being achieved regardless of the steric and electronic properties of the substrates. This method therefore offers promising synthetic routes for the construction of a library of optically active 1,5-benzothiazepines for assay evaluation.

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    3. Takumaru Kurihara, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga. Achiral Cp*Rh(III)/Chiral Lewis Base Cooperative Catalysis for Enantioselective Cyclization via C–H Activation. Journal of the American Chemical Society 2022, 144 (16) , 7058-7065. https://doi.org/10.1021/jacs.2c01223
    4. Lijie Zhang, Ling Fang, Hao Huang, Chaofan Wang, Fang Gao, Zhiyong Wang. Synthesis of Benzo[e][1,4]thiazepines by Base-Induced Formal [4+3] Annulation Reaction of Aza-o-quinone Methides and Pyridinium 1,4-Zwitterionic Thiolates. The Journal of Organic Chemistry 2021, 86 (24) , 18156-18163. https://doi.org/10.1021/acs.joc.1c02433
    5. Dawei Li, Sijing Wang, Shulin Ge, Shunxi Dong, Xiaoming Feng. Asymmetric Synthesis of Axially Chiral Anilides via Organocatalytic Atroposelective N-Acylation. Organic Letters 2020, 22 (14) , 5331-5336. https://doi.org/10.1021/acs.orglett.0c01581
    6. Anil K. Pandey, Steven E. Kirberger, Jorden A. Johnson, Jennifer R. Kimbrough, Danika K. D. Partridge, William C. K. Pomerantz. Efficient Synthesis of 1,4-Thiazepanones and 1,4-Thiazepanes as 3D Fragments for Screening Libraries. Organic Letters 2020, 22 (10) , 3946-3950. https://doi.org/10.1021/acs.orglett.0c01230
    7. Yu-Chen Zhang, Rui-Long Geng, Jin Song, Liu-Zhu Gong. Isothiourea and Brønsted Acid Cooperative Catalysis: Enantioselective Construction of Dihydropyridinones. Organic Letters 2020, 22 (6) , 2261-2265. https://doi.org/10.1021/acs.orglett.0c00461
    8. Honglei Liu, Alexandra M. Z. Slawin, Andrew D. Smith. Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones. Organic Letters 2020, 22 (4) , 1301-1305. https://doi.org/10.1021/acs.orglett.9b04615
    9. Ling Meng, Ka Yan Ngai, Xiaoyong Chang, Zhenyang Lin, Jun Wang. Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones. Organic Letters 2020, 22 (3) , 1155-1159. https://doi.org/10.1021/acs.orglett.0c00005
    10. Congcong Yin, Tao Yang, Yingmin Pan, Jialin Wen, Xumu Zhang. Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones. Organic Letters 2020, 22 (3) , 920-923. https://doi.org/10.1021/acs.orglett.9b04478
    11. Changyi Liu, Shuquan Wu, Jun Xu, Lingzhu Chen, Pengcheng Zheng, Yonggui Robin Chi. Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles. Organic Letters 2019, 21 (23) , 9493-9496. https://doi.org/10.1021/acs.orglett.9b03685
    12. Chun-Lin Zhang, Zhao-Fei Zhang, Zi-Hao Xia, You-Feng Han, Song Ye. DBU-Mediated Construction of 1,3,5-Trisubstituted Benzenes via Annulation of α,β-Unsaturated Carboxylic Acids and α-Cyano-β-methylenones. The Journal of Organic Chemistry 2018, 83 (20) , 12507-12513. https://doi.org/10.1021/acs.joc.8b01740
    13. Wei-Si Guo, Hao Gong, Yan-An Zhang, Li-Rong Wen, Ming Li. Fast Construction of 1,3-Benzothiazepines by Direct Intramolecular Dehydrogenative C–S Bond Formation of Thioamides under Metal-Free Conditions. Organic Letters 2018, 20 (20) , 6394-6397. https://doi.org/10.1021/acs.orglett.8b02697
    14. Noboru Hayama, Ryuta Kuramoto, Tamás Földes, Kazuya Nishibayashi, Yusuke Kobayashi, Imre Pápai, Yoshiji Takemoto. Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas. Journal of the American Chemical Society 2018, 140 (38) , 12216-12225. https://doi.org/10.1021/jacs.8b07511
    15. Keisuke Asano, Seijiro Matsubara. Catalytic Approaches to Optically Active 1,5-Benzothiazepines. ACS Catalysis 2018, 8 (7) , 6273-6282. https://doi.org/10.1021/acscatal.8b00908
    16. Khoi N. Van and Daniel Romo . Multicomponent, Enantioselective Michael–Michael-Aldol-β-Lactonizations Delivering Complex β-Lactones. The Journal of Organic Chemistry 2018, 83 (2) , 632-643. https://doi.org/10.1021/acs.joc.7b02543
    17. Jing Cao, Kewen Sun, Shuding Dong, Tao Lu, Ying Dong, and Ding Du . Esters as Alkynyl Acyl Ammonium and Azolium Precursors: A Formal [2 + 3] Annulation with Amidomalonates via Lewis Base/Lewis Acid Cooperative Catalysis. Organic Letters 2017, 19 (24) , 6724-6727. https://doi.org/10.1021/acs.orglett.7b03453
    18. Yukihiro Fukata, Koichi Yao, Ryota Miyaji, Keisuke Asano, and Seijiro Matsubara . Asymmetric Net Cycloaddition for Access to Diverse Substituted 1,5-Benzothiazepines. The Journal of Organic Chemistry 2017, 82 (23) , 12655-12668. https://doi.org/10.1021/acs.joc.7b02451
    19. Hong Lu, Jia-Lu Zhang, Jin-Yu Liu, Hong-Yu Li, and Peng-Fei Xu . N-Heterocyclic Carbene-Catalyzed Atom-Economical and Enantioselective Construction of the C–S Bond: Asymmetric Synthesis of Functionalized Thiochromans. ACS Catalysis 2017, 7 (11) , 7797-7802. https://doi.org/10.1021/acscatal.7b02651
    20. Chao Fang, Tao Lu, Jindong Zhu, Kewen Sun, and Ding Du . Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H-Free 1,5-Benzothiazepines. Organic Letters 2017, 19 (13) , 3470-3473. https://doi.org/10.1021/acs.orglett.7b01457
    21. Shoulei Wang, Javier Izquierdo, Carles Rodríguez-Escrich, and Miquel A. Pericàs . Asymmetric [4 + 2] Annulation Reactions Catalyzed by a Robust, Immobilized Isothiourea. ACS Catalysis 2017, 7 (4) , 2780-2785. https://doi.org/10.1021/acscatal.7b00360
    22. Jian-Qiang Chen, Wan-Lei Yu, Yun-Long Wei, Teng-Hui Li, and Peng-Fei Xu . Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines. The Journal of Organic Chemistry 2017, 82 (1) , 243-249. https://doi.org/10.1021/acs.joc.6b02377
    23. Alexander S. Mikherdov, Mikhail A. Kinzhalov, Alexander S. Novikov, Vadim P. Boyarskiy, Irina A. Boyarskaya, Dmitry V. Dar’in, Galina L. Starova, and Vadim Yu. Kukushkin . Difference in Energy between Two Distinct Types of Chalcogen Bonds Drives Regioisomerization of Binuclear (Diaminocarbene)PdII Complexes. Journal of the American Chemical Society 2016, 138 (42) , 14129-14137. https://doi.org/10.1021/jacs.6b09133
    24. Ling Meng, Ming Yu Jin, and Jun Wang . Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones. Organic Letters 2016, 18 (19) , 4986-4989. https://doi.org/10.1021/acs.orglett.6b02453
    25. Nicholas A. Ahlemeyer and Vladimir B. Birman . Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl Transfer-Initiated Cascade. Organic Letters 2016, 18 (14) , 3454-3457. https://doi.org/10.1021/acs.orglett.6b01639
    26. Ajaz A. Dar, M. Shadab, Suman Khan, Nahid Ali, and Abu T. Khan . One-Pot Synthesis and Evaluation of Antileishmanial Activities of Functionalized S-Alkyl/Aryl Benzothiazole-2-carbothioate Scaffold. The Journal of Organic Chemistry 2016, 81 (8) , 3149-3160. https://doi.org/10.1021/acs.joc.6b00113
    27. Javier Izquierdo and Miquel A. Pericàs . A Recyclable, Immobilized Analogue of Benzotetramisole for Catalytic Enantioselective Domino Michael Addition/Cyclization Reactions in Batch and Flow. ACS Catalysis 2016, 6 (1) , 348-356. https://doi.org/10.1021/acscatal.5b02121
    28. Kazuki Maeda, Takuma Terada, Takahiro Iwamoto, Takuya Kurahashi, and Seijiro Matsubara . Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes. Organic Letters 2015, 17 (21) , 5284-5287. https://doi.org/10.1021/acs.orglett.5b02654
    29. Ximin Li, Hui Jiang, Vladimir B. Birman. 2,3‐Dihydro‐2‐phenylimidazo[2,1‐ b ]benzothiazole (BTM). 2025, 1-12. https://doi.org/10.1002/047084289X.rn00976.pub3
    30. Katarina Magdalenic, Donatien Morillon, Steven De Jonghe, Leentje Persoons, Dominique Schols, Kristof Van Hecke, Charlotte Grootaert, John Van Camp, Matthias D'hooghe. Synthesis and Cancer Cell Cytotoxicity of 6‐, 7‐, or 8‐Substituted 2‐(Hetero)aryl‐4‐(4‐(Hetero)aryl‐2‐Oxobut‐3‐en‐1‐Ylidene)Benzothiazepanes. Journal of Heterocyclic Chemistry 2024, https://doi.org/10.1002/jhet.4936
    31. Sarita G. Kundlikar, Hemantkumar N. Akolkar, Dilip R. Thube, Nirmala R. Darekar, Vijay M. Khedkar. Benzothiazepine. 2024, 349-374. https://doi.org/10.4018/979-8-3693-7520-4.ch011
    32. Danyang Xie, Sishi Zhong, Yong Xia. Asymmetric Synthesis of Seven‐Membered Lactams: Recent Advances and Future Perspectives. European Journal of Organic Chemistry 2024, 27 (41) https://doi.org/10.1002/ejoc.202400687
    33. Yijun Shi, Guoli Yan, Shuo Yin, Han Cao, Fusheng Bie, Jie Xiong. Thioesterification and Hydrothiolation of α, β‐ Unsaturated Esters with Aliphatic Thiols under Mild Conditions. ChemistrySelect 2024, 9 (39) https://doi.org/10.1002/slct.202402479
    34. Zhongfu Luo, Minghong Liao, Wei Li, Sha Zhao, Kun Tang, Pengcheng Zheng, Yonggui Robin Chi, Xinglong Zhang, Xingxing Wu. Ionic Hydrogen Bond‐Assisted Catalytic Construction of Nitrogen Stereogenic Center via Formal Desymmetrization of Remote Diols. Angewandte Chemie 2024, 136 (31) https://doi.org/10.1002/ange.202404979
    35. Zhongfu Luo, Minghong Liao, Wei Li, Sha Zhao, Kun Tang, Pengcheng Zheng, Yonggui Robin Chi, Xinglong Zhang, Xingxing Wu. Ionic Hydrogen Bond‐Assisted Catalytic Construction of Nitrogen Stereogenic Center via Formal Desymmetrization of Remote Diols. Angewandte Chemie International Edition 2024, 63 (31) https://doi.org/10.1002/anie.202404979
    36. Hongyan Long, Sha Zhao, Chunyan Jian, Xiuli Wu, Fengfei Lu, Minghong Liao, Fengrui Che, Xingxing Wu, Yonggui Robin Chi. Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles. Science China Chemistry 2024, 67 (7) , 2199-2205. https://doi.org/10.1007/s11426-023-1909-5
    37. Katarina Magdalenić, Felien Morlion, Steven De Jonghe, Leentje Persoons, Dominique Schols, Charlotte Grootaert, John Van Camp, Matthias D'hooghe. Synthesis and cancer cell cytotoxicity of 2-heteroaryl-4-(4-heteroaryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes. Tetrahedron 2024, 5 , 133884. https://doi.org/10.1016/j.tet.2024.133884
    38. Ding Yuan, Alister S. Goodfellow, Kevin Kasten, Zhuan Duan, Tengfei Kang, David B. Cordes, Aidan P. McKay, Michael Bühl, Gregory R. Boyce, Andrew D. Smith. Understanding divergent substrate stereoselectivity in the isothiourea-catalysed conjugate addition of cyclic α-substituted β-ketoesters to α,β-unsaturated aryl esters. Chemical Science 2023, 14 (48) , 14146-14156. https://doi.org/10.1039/D3SC05470E
    39. Ashok Kumar Suman, Anu Dushad, Bhawani Singh. 1,5-Benzothiazepines: Recent developments in the synthetic strategies. Tetrahedron 2023, 142 , 133513. https://doi.org/10.1016/j.tet.2023.133513
    40. Cheng Niu, Da‐Ming Du. Recent Advances in Organocatalyzed Asymmetric Sulfa‐Michael Addition Triggered Cascade Reactions. The Chemical Record 2023, 23 (7) https://doi.org/10.1002/tcr.202200258
    41. Roman A. Popov, Alexander S. Novikov, Vitalii V. Suslonov, Vadim P. Boyarskiy. Molecular Switching through Chalcogen-Bond-Induced Isomerization of Binuclear (Diaminocarbene)PdII Complexes. Inorganics 2023, 11 (6) , 255. https://doi.org/10.3390/inorganics11060255
    42. Katarina Magdalenić, Ulrike Ronse, Steven De Jonghe, Leentje Persoons, Dominique Schols, Julie De Munck, Charlotte Grootaert, John Van Camp, Matthias D’hooghe. Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes. Phytochemistry Letters 2023, 55 , 117-123. https://doi.org/10.1016/j.phytol.2023.04.008
    43. Wei Tan, Jia-Yi Zhang, Cong-Hui Gao, Feng Shi. Progress in organocatalytic asymmetric (4+3) cycloadditions for the enantioselective construction of seven-membered rings. Science China Chemistry 2023, 66 (4) , 966-992. https://doi.org/10.1007/s11426-022-1471-2
    44. Fenghai Guo, Jayla A. Young, Mina S. Perez, Holden A. Hankerson, Alex M. Chavez. Progress on the Cu-Catalyzed 1,4-Conjugate Addition to Thiochromones. Catalysts 2023, 13 (4) , 713. https://doi.org/10.3390/catal13040713
    45. Tim Steinke, Stefan M. Huber. Chalcogen Bond Donors in Organic Synthesis. 2023, 529-549. https://doi.org/10.1039/BK9781839167386-00529
    46. Abdikani Omar Farah, Jorge Garcia, Claire Borg, Timothy K. Beng. Serendipitous synthesis of cross-conjugated dienes by cascade deconstructive esterification of thiomorpholinone-tethered alkenoic acids. RSC Advances 2023, 13 (5) , 3181-3185. https://doi.org/10.1039/D2RA07916J
    47. Alastair J. Nimmo, Claire M. Young, Andrew D. Smith. Isothiourea Catalysis – New Opportunities for Asymmetric Synthesis. 2023, 151-202. https://doi.org/10.1002/9783527832217.ch5
    48. Jianjian Liu, Mali Zhou, Rui Deng, Pengcheng Zheng, Yonggui Robin Chi. Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-32428-4
    49. Timothy K. Beng, Mckenna Sax, Claire Borg. Serendipitous synthesis of 2-alkenyl- and 2-aryl-4-thiazolidinones using dithiodiglycolic anhydride. New Journal of Chemistry 2022, 46 (38) , 18505-18511. https://doi.org/10.1039/D2NJ03719J
    50. Ángel Cores, Mercedes Villacampa, J. Carlos Menéndez. Organocatalysis in Synthetic Heterocyclic Chemistry. 2022, 85-115. https://doi.org/10.1002/9783527832002.ch4
    51. Moritz E. Hansen, Samuel O. Yasmin, Susanne Wolfrum, Erick M. Carreira. Total Synthesis of Mutanobactins A, B from the Human Microbiome: Macrocyclization and Thiazepanone Assembly in a Single Step. Angewandte Chemie 2022, 134 (28) https://doi.org/10.1002/ange.202203051
    52. Moritz E. Hansen, Samuel O. Yasmin, Susanne Wolfrum, Erick M. Carreira. Total Synthesis of Mutanobactins A, B from the Human Microbiome: Macrocyclization and Thiazepanone Assembly in a Single Step. Angewandte Chemie International Edition 2022, 61 (28) https://doi.org/10.1002/anie.202203051
    53. Chuan‐Chuan Wang, Xue‐Hua Liu, Xin‐Lu Wang, Hua‐Peng Cui, Zhi‐Wei Ma, Degang Ding, Jun‐Tao Liu, Lei Meng, Ya‐Jing Chen. Synthesis of Functionalized 4,1‐Benzothiazepines via a [4+3] Annulation between Aza‐ o‐ Quinone Methides and Pyridinium 1,4‐Zwitterionic Thiolates. Advanced Synthesis & Catalysis 2022, 364 (2) , 296-301. https://doi.org/10.1002/adsc.202101034
    54. Alexander Sapegin, Elena Reutskaya, Mikhail Krasavin. 1,4-Oxazepines and 1,4-Thiazepines. 2022, 313-370. https://doi.org/10.1016/B978-0-12-818655-8.00077-9
    55. Farzad Zamani, Esmail Doustkhah, Fatemeh Ahmadi, Rajender S. Varma. Synthesis of 1,5-benzodiazepines and 1,5-benzothiazepines. 2022, 199-248. https://doi.org/10.1016/B978-0-12-824516-3.00003-3
    56. Heather Lam, Xavier Abel-Snape, Martin Köllen, Mark Lautens. (4 + 1), (4 + 3) and (4 + 4) Cycloadditions and Annulations. 2022https://doi.org/10.1016/B978-0-32-390644-9.00048-2
    57. Heather Lam, Xavier Abel-Snape, Martin F. Köllen, Mark Lautens. Recent Advances in Transition-Metal-Free (4+3)-Annulations. Synthesis 2021, 53 (22) , 4134-4177. https://doi.org/10.1055/s-0040-1706023
    58. Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi. Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances. Advanced Synthesis & Catalysis 2021, 363 (14) , 3380-3410. https://doi.org/10.1002/adsc.202100006
    59. Jacqueline Bitai, Matthew T. Westwood, Andrew D. Smith. α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update. Organic & Biomolecular Chemistry 2021, 19 (11) , 2366-2384. https://doi.org/10.1039/D0OB02208J
    60. Atash V. Gurbanov, Maxim L. Kuznetsov, Kamran T. Mahmudov, Armando J. L. Pombeiro, Giuseppe Resnati. Resonance Assisted Chalcogen Bonding as a New Synthon in the Design of Dyes. Chemistry – A European Journal 2020, 26 (65) , 14833-14837. https://doi.org/10.1002/chem.202002518
    61. Anup Biswas, Haripriyo Mondal, Modhu S. Maji. Synthesis of Heterocycles by isothiourea organocatalysis. Journal of Heterocyclic Chemistry 2020, 57 (11) , 3818-3844. https://doi.org/10.1002/jhet.4119
    62. Kamran T. Mahmudov, M. Fátima C. Guedes da Silva, Atash V. Gurbanov, Armando J. L. Pombeiro. Noncovalent Interactions in N ‐Heterocyclic Chemistry. 2020, 767-787. https://doi.org/10.1002/9781119708841.ch24
    63. Varsha Devi, Gurpreet Singh, Vikramdeep Monga. Recent advances in the synthetic chemistry of 1,5 ‐benzothiazepines : A minireview. Journal of Heterocyclic Chemistry 2020, 57 (9) , 3255-3270. https://doi.org/10.1002/jhet.4062
    64. Noboru Hayama, Yusuke Kobayashi, Eriko Sekimoto, Anna Miyazaki, Kiyofumi Inamoto, Tetsutaro Kimachi, Yoshiji Takemoto. A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst. Chemical Science 2020, 11 (21) , 5572-5576. https://doi.org/10.1039/D0SC01729A
    65. Haifeng Wang, Shuangxi Gu, Qiongjiao Yan, Li Ding, Fen-Er Chen. Asymmetric catalysis in synthetic strategies for chiral benzothiazepines. Green Synthesis and Catalysis 2020, 1 (1) , 12-25. https://doi.org/10.1016/j.gresc.2020.05.005
    66. Tania J. Bellinger, Teavian Harvin, Ti’Bran Pickens-Flynn, Nataleigh Austin, Samuel H. Whitaker, Mai Ling C. Tang Yuk Tutein, Dabria T. Hukins, Nichele Deese, Fenghai Guo. Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone. Molecules 2020, 25 (9) , 2128. https://doi.org/10.3390/molecules25092128
    67. Subhajit Pramanik, Deepak Chopra. Unravelling the Importance of H bonds, σ–hole and π–hole-Directed Intermolecular Interactions in Nature. Journal of the Indian Institute of Science 2020, 100 (1) , 43-59. https://doi.org/10.1007/s41745-019-00144-6
    68. Chang Shu, Honglei Liu, Alexandra M. Z. Slawin, Cameron Carpenter-Warren, Andrew D. Smith. Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters. Chemical Science 2020, 11 (1) , 241-247. https://doi.org/10.1039/C9SC04303A
    69. Muxing Zhou, Ende He, Lu Zhang, Jianzhong Chen, Zhenfeng Zhang, Yangang Liu, Wanbin Zhang. Development of a new bicyclic imidazole nucleophilic organocatalyst for direct enantioselective C -acylation. Organic Chemistry Frontiers 2019, 6 (24) , 3969-3972. https://doi.org/10.1039/C9QO01025D
    70. Julia Bamberger, Florian Ostler, Olga García Mancheño. Frontiers in Halogen and Chalcogen‐Bond Donor Organocatalysis. ChemCatChem 2019, 11 (21) , 5198-5211. https://doi.org/10.1002/cctc.201901215
    71. Lu‐Lu Li, Du Ding, Jin Song, Zhi‐Yong Han, Liu‐Zhu Gong. Catalytic Generation of C1 Ammonium Enolates from Halides and CO for Asymmetric Cascade Reactions. Angewandte Chemie 2019, 131 (23) , 7729-7733. https://doi.org/10.1002/ange.201901501
    72. Lu‐Lu Li, Du Ding, Jin Song, Zhi‐Yong Han, Liu‐Zhu Gong. Catalytic Generation of C1 Ammonium Enolates from Halides and CO for Asymmetric Cascade Reactions. Angewandte Chemie International Edition 2019, 58 (23) , 7647-7651. https://doi.org/10.1002/anie.201901501
    73. N. Dennis. Addition Reactions: Cycloaddition. 2019, 517-566. https://doi.org/10.1002/9781119125082.ch11
    74. Mohamed Ali Ben Aissa, Sabri Hassen, Youssef Arfaoui. Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX 2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes. International Journal of Quantum Chemistry 2019, 119 (6) https://doi.org/10.1002/qua.25837
    75. Lukas Vogel, Patrick Wonner, Stefan M. Huber. Chalkogenbrücken: eine Übersicht. Angewandte Chemie 2019, 131 (7) , 1896-1907. https://doi.org/10.1002/ange.201809432
    76. Lukas Vogel, Patrick Wonner, Stefan M. Huber. Chalcogen Bonding: An Overview. Angewandte Chemie International Edition 2019, 58 (7) , 1880-1891. https://doi.org/10.1002/anie.201809432
    77. Abel M. Maharramov, Namiq Q. Shikhaliyev, Gulnar T. Suleymanova, Atash V. Gurbanov, Gulnara V. Babayeva, Gunay Z. Mammadova, Fedor I. Zubkov, Valentine G. Nenajdenko, Kamran T. Mahmudov, Armando J.L. Pombeiro. Pnicogen, halogen and hydrogen bonds in (E)-1-(2,2-dichloro-1-(2-nitrophenyl)vinyl)-2-(para-substituted phenyl)-diazenes. Dyes and Pigments 2018, 159 , 135-141. https://doi.org/10.1016/j.dyepig.2018.06.022
    78. Yi Huang, Pan Li, Xiu-Qin Dong, Xumu Zhang. Synthesis of chiral seven-membered β-substituted lactams via Rh-catalyzed asymmetric hydrogenation. Organic & Biomolecular Chemistry 2018, 16 (45) , 8819-8823. https://doi.org/10.1039/C8OB02231C
    79. Jing-Hai Jin, Xiang-Yu Li, Xiaoyan Luo, Wei-Ping Deng. Enantioselective synthesis of indolo[2,3-b]-dihydrothiopyranones via [3+3] cycloaddition of chiral α,β-unsaturated acylammonium salts. Tetrahedron 2018, 74 (47) , 6804-6808. https://doi.org/10.1016/j.tet.2018.09.024
    80. Shekinah A. Bass, Dynasty M. Parker, Tania J. Bellinger, Aireal S. Eaton, Angelica S. Dibble, Kaata L. Koroma, Sylvia A. Sekyi, David A. Pollard, Fenghai Guo. Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications. Molecules 2018, 23 (7) , 1728. https://doi.org/10.3390/molecules23071728
    81. Zhao‐Fei Zhang, Chun‐Lin Zhang, Zhi‐Yong Song, Zhong‐Hua Gao, Song Ye. N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones. Chemistry – A European Journal 2018, 24 (33) , 8302-8305. https://doi.org/10.1002/chem.201801539
    82. Mei‐Xin Zhao, Min Shi. Organoamines‐catalyzed Cycloadditions. 2018, 25-140. https://doi.org/10.1002/9783527807291.ch2
    83. Guowei Kang, Masaki Yamagami, Sreekumar Vellalath, Daniel Romo. Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts. Angewandte Chemie 2018, 130 (22) , 6637-6641. https://doi.org/10.1002/ange.201802483
    84. Guowei Kang, Masaki Yamagami, Sreekumar Vellalath, Daniel Romo. Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts. Angewandte Chemie International Edition 2018, 57 (22) , 6527-6531. https://doi.org/10.1002/anie.201802483
    85. Eder João Lenardão, Claudio Santi, Luca Sancineto. Nonbonded Interaction: The Chalcogen Bond. 2018, 157-183. https://doi.org/10.1007/978-3-319-92405-2_4
    86. Fanghui Ma, Jing Qian, Ping Lu, Yanguang Wang. Convenient synthesis of 2-amino-3-(arylthio)indoles via the Rh-catalyzed reaction of 3-diazoindol-2-imines with thioesters. Organic & Biomolecular Chemistry 2018, 16 (3) , 439-443. https://doi.org/10.1039/C7OB02597A
    87. Sara Meninno, Ilaria Quaratesi, Chiara Volpe, Andrea Mazzanti, Alessandra Lattanzi. Catalytic enantioselective one-pot approach to cis - and trans -2,3-diaryl substituted 1,5-benzothiazepines. Organic & Biomolecular Chemistry 2018, 16 (38) , 6923-6934. https://doi.org/10.1039/C8OB01988F
    88. Mark D. Greenhalgh, Shen Qu, Alexandra M. Z. Slawin, Andrew D. Smith. Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis. Chemical Science 2018, 9 (21) , 4909-4918. https://doi.org/10.1039/C8SC01324A
    89. Firudin Guseinov, Mikhail Pistsov, Eldar Movsumzade, Leonid Kustov, Victor Tafeenko, Vladimir Chernyshev, Atash Gurbanov, Kamran Mahmudov, Armando Pombeiro. Tetrel, Chalcogen, and Charge-Assisted Hydrogen Bonds in 2-((2-Carboxy-1-(substituted)-2-hydroxyethyl)thio) Pyridin-1-ium Chlorides. Crystals 2017, 7 (11) , 327. https://doi.org/10.3390/cryst7110327
    90. Anastassia Matviitsuk, Mark D. Greenhalgh, Diego‐Javier Barrios Antúnez, Alexandra M. Z. Slawin, Andrew D. Smith. Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis. Angewandte Chemie 2017, 129 (40) , 12450-12455. https://doi.org/10.1002/ange.201706402
    91. Anastassia Matviitsuk, Mark D. Greenhalgh, Diego‐Javier Barrios Antúnez, Alexandra M. Z. Slawin, Andrew D. Smith. Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis. Angewandte Chemie International Edition 2017, 56 (40) , 12282-12287. https://doi.org/10.1002/anie.201706402
    92. Fenghai Guo, Malcolm C. Jeffries, Briana N. Graves, Shekinah A. Graham, David A. Pollard, Gehao Pang, Henry Y. Chen. A rapid entry into thioflavanones via conjugate additions of diarylcuprates to thiochromones. Tetrahedron 2017, 73 (39) , 5745-5750. https://doi.org/10.1016/j.tet.2017.08.012
    93. Sara Meninno, Chiara Volpe, Alessandra Lattanzi. Catalytic Enantioselective Synthesis of Protecting‐Group‐Free 1,5‐Benzothiazepines. Chemistry – A European Journal 2017, 23 (19) , 4547-4550. https://doi.org/10.1002/chem.201700837
    94. Guojin Wang, Yu Tang, Yu Zhang, Xiaohua Liu, Lili Lin, Xiaoming Feng. Enantioselective Synthesis of N−H‐Free 1,5‐Benzothiazepines. Chemistry – A European Journal 2017, 23 (3) , 554-557. https://doi.org/10.1002/chem.201605127
    95. Vasco Corti, Patricia Camarero Gonzalez, Julie Febvay, Lorenzo Caruana, Andrea Mazzanti, Mariafrancesca Fochi, Luca Bernardi. Organocatalytic Asymmetric Sulfa‐Michael Addition of 2‐Aminothiophenols to Chalcones: First Enantioselective Access to 2,3,4,5‐Tetrahydro‐1,5‐benzothiazepines. European Journal of Organic Chemistry 2017, 2017 (1) , 49-52. https://doi.org/10.1002/ejoc.201601364
    96. Mikail E. Abbasov, Brandi M. Hudson, Weixu Kong, Dean J. Tantillo, Daniel Romo. Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene. Organic & Biomolecular Chemistry 2017, 15 (15) , 3179-3183. https://doi.org/10.1039/C6OB02738E
    97. Mikail E. Abbasov, Brandi M. Hudson, Dean J. Tantillo, Daniel Romo. Stereodivergent, Diels–Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application. Chemical Science 2017, 8 (2) , 1511-1524. https://doi.org/10.1039/C6SC04273B
    98. Kamran T. Mahmudov, Maximilian N. Kopylovich, M. Fátima C. Guedes da Silva, Armando J. L. Pombeiro. Chalcogen bonding in synthesis, catalysis and design of materials. Dalton Transactions 2017, 46 (31) , 10121-10138. https://doi.org/10.1039/C7DT01685A
    99. Anastassia Matviitsuk, James E. Taylor, David B. Cordes, Alexandra M. Z. Slawin, Andrew D. Smith. Enantioselective Stereodivergent Nucleophile‐Dependent Isothiourea‐Catalysed Domino Reactions. Chemistry – A European Journal 2016, 22 (49) , 17748-17757. https://doi.org/10.1002/chem.201603318
    100. Jérémy Merad, Jean‐Marc Pons, Olivier Chuzel, Cyril Bressy. Enantioselective Catalysis by Chiral Isothioureas. European Journal of Organic Chemistry 2016, 2016 (34) , 5589-5610. https://doi.org/10.1002/ejoc.201600399
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    Published April 9, 2015
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