Nucleophilic opening of 2,3-epoxy acids and amides mediated by titanium isopropoxide. Highly enhanced C-3 selectivity

Click to copy article linkArticle link copied!

This article is cited by 186 publications.

1. Shan-Shan Xun, Han Wang, Chang-Bin Yu, Sheng-Mei Lu, Yong-Gui Zhou. Diarylborinic Acid-Catalyzed Ring Opening of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides: Synthesis of 1,2,4-Trisubstituted Cyclopentanes. Organic Letters 2023, 25 (41) , 7540-7544. https://doi.org/10.1021/acs.orglett.3c02886
2. Someshwar Nagamalla, Joel T. Mague, Shyam Sathyamoorthi. Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides. Organic Letters 2023, 25 (6) , 982-986. https://doi.org/10.1021/acs.orglett.3c00053
3. Someshwar Nagamalla, Debobrata Paul, Joel T. Mague, Shyam Sathyamoorthi. Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine. Organic Letters 2022, 24 (33) , 6202-6207. https://doi.org/10.1021/acs.orglett.2c02496
4. Someshwar Nagamalla, Joel T. Mague, Shyam Sathyamoorthi. Ring Opening of Epoxides by Pendant Silanols. Organic Letters 2022, 24 (3) , 939-943. https://doi.org/10.1021/acs.orglett.1c04310
5. Shrey P. Desai, Mark S. Taylor. Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles. Organic Letters 2021, 23 (18) , 7049-7054. https://doi.org/10.1021/acs.orglett.1c02412
6. Aran K. Hubbell, Geoffrey W. Coates. Nucleophilic Transformations of Lewis Acid-Activated Disubstituted Epoxides with Catalyst-Controlled Regioselectivity. The Journal of Organic Chemistry 2020, 85 (21) , 13391-13414. https://doi.org/10.1021/acs.joc.0c01691
7. Shun-ichiro Uesugi, Tsubasa Watanabe, Takamichi Imaizumi, Yu Ota, Keisuke Yoshida, Haruna Ebisu, Takumi Chinen, Yoko Nagumo, Masatoshi Shibuya, Naoki Kanoh, Takeo Usui, and Yoshiharu Iwabuchi . Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B. The Journal of Organic Chemistry 2015, 80 (24) , 12333-12350. https://doi.org/10.1021/acs.joc.5b02256
8. Goreti Rajendar and E. J. Corey . A Systematic Study of Functionalized Oxiranes as Initiating Groups for Cationic Polycyclization Reactions. Journal of the American Chemical Society 2015, 137 (17) , 5837-5844. https://doi.org/10.1021/jacs.5b03229
9. Shun-ichiro Uesugi, Tsubasa Watanabe, Takamichi Imaizumi, Masatoshi Shibuya, Naoki Kanoh, and Yoshiharu Iwabuchi . Eu(OTf)3-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives. Organic Letters 2014, 16 (17) , 4408-4411. https://doi.org/10.1021/ol502264y
10. Palakodety Radha Krishna and D. Venkata Ramana . Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides. The Journal of Organic Chemistry 2012, 77 (1) , 674-679. https://doi.org/10.1021/jo202199g
11. Toshimasa Katagiri, Yousuke Katayama, Mayuko Taeda, Takanori Ohshima, Naomi Iguchi, and Kenji Uneyama . Preparation of Optically Pure α-Trifluoromethyl-α-amino Acids from N-Tosyl-2-trifluoromethyl-2-alkyloxycarbonyl Aziridine. The Journal of Organic Chemistry 2011, 76 (22) , 9305-9311. https://doi.org/10.1021/jo201554g
12. Farhad Nowrouzi, John Janetzko, and Robert A. Batey. Indium-Promoted Chemo- and Diastereoselective Allylation of α,β-Epoxy Ketones with Potassium Allyltrifluoroborate. Organic Letters 2010, 12 (23) , 5490-5493. https://doi.org/10.1021/ol1023757
13. K. C. Nicolaou, Xiao-Shui Peng, Ya-Ping Sun, Damien Polet, Bin Zou, Chek Shik Lim and David Y.-K. Chen. Total Synthesis and Biological Evaluation of Cortistatins A and J and Analogues Thereof. Journal of the American Chemical Society 2009, 131 (30) , 10587-10597. https://doi.org/10.1021/ja902939t
14. Aélig Robin,, Fraser Brown,, Noemí Bahamontes-Rosa,, Binghua Wu,, Eric Beitz,, Jürgen F. J. Kun, and, Sabine L. Flitsch. Microwave-Assisted Ring Opening of Epoxides:  A General Route to the Synthesis of 1-Aminopropan-2-ols with Anti Malaria Parasite Activities. Journal of Medicinal Chemistry 2007, 50 (17) , 4243-4249. https://doi.org/10.1021/jm070553l
15. Yoshiyasu Ichikawa,, Haruka Egawa,, Takashi Ito,, Minoru Isobe,, Keiji Nakano, and, Hiyoshizo Kotsuki. Stereocontrolled Route to Vicinal Diamines by [3.3] Sigmatropic Rearrangement of Allyl Cyanate:  Asymmetric Synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-Diaminobutanoic Acids. Organic Letters 2006, 8 (25) , 5737-5740. https://doi.org/10.1021/ol0621102
16. Xiaoguang Lei and, John A. Porco, Jr.. Total Synthesis of the Diazobenzofluorene Antibiotic (−)-Kinamycin C. Journal of the American Chemical Society 2006, 128 (46) , 14790-14791. https://doi.org/10.1021/ja066621v
17. Odile Meyer,, Sarah Ponaire,, Michel Rohmer, and, Catherine Grosdemange-Billiard. Lewis Acid Mediated Regioselective Ring Opening of Benzylglycidol with Dibenzyl Phosphate:  Short and Attractive Synthesis of Dihydroxyacetone Phosphate. Organic Letters 2006, 8 (19) , 4347-4350. https://doi.org/10.1021/ol061748a
18. Jenny K. Ekegren,, Torsten Unge,, Mayada Zreik Safa,, Hans Wallberg,, Bertil Samuelsson, and, Anders Hallberg. A New Class of HIV-1 Protease Inhibitors Containing a Tertiary Alcohol in the Transition-State Mimicking Scaffold. Journal of Medicinal Chemistry 2005, 48 (25) , 8098-8102. https://doi.org/10.1021/jm050790t
19. Francesco Fringuelli,, Ferdinando Pizzo,, Simone Tortoioli, and, Luigi Vaccaro. InCl3-Catalyzed Regio- and Stereoselective Thiolysis of α,β-Epoxycarboxylic Acids in Water. Organic Letters 2005, 7 (20) , 4411-4414. https://doi.org/10.1021/ol051582y
20. Mei-Xiang Wang,, Gang Deng,, De-Xian Wang, and, Qi-Yu Zheng. Nitrile Biotransformations for Highly Enantioselective Synthesis of Oxiranecarboxamides with Tertiary and Quaternary Stereocenters; Efficient Chemoenzymatic Approaches to Enantiopure α-Methylated Serine and Isoserine Derivatives. The Journal of Organic Chemistry 2005, 70 (7) , 2439-2444. https://doi.org/10.1021/jo0482615
21. Shin-ya Tosaki,, Riichiro Tsuji,, Takashi Ohshima, and, Masakatsu Shibasaki. Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process. Journal of the American Chemical Society 2005, 127 (7) , 2147-2155. https://doi.org/10.1021/ja043770+
22. Francesco Fringuelli,, Ferdinando Pizzo,, Mauro Rucci, and, Luigi Vaccaro. First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines. The Journal of Organic Chemistry 2003, 68 (18) , 7041-7045. https://doi.org/10.1021/jo034752y
23. Anna Mühlman,, Björn Classon,, Anders Hallberg, and, Bertil Samuelsson. Synthesis of Potent C2-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents. Journal of Medicinal Chemistry 2001, 44 (21) , 3402-3406. https://doi.org/10.1021/jm0011169
24. David Amantini,, Francesco Fringuelli,, Ferdinando Pizzo, and, Luigi Vaccaro. Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides. The Journal of Organic Chemistry 2001, 66 (13) , 4463-4467. https://doi.org/10.1021/jo0156215
25. Francesco Fringuelli,, Ferdinando Pizzo, and, Luigi Vaccaro. Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0. The Journal of Organic Chemistry 2001, 66 (10) , 3554-3558. https://doi.org/10.1021/jo015564f
26. Kiyoshi Nakayama,, Haruko C. Kawato,, Hiroaki Inagaki,, Ryohei Nakajima,, Akihiro Kitamura,, Kazuhiko Someya, and, Toshiharu Ohta. Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid Moiety. Organic Letters 2000, 2 (7) , 977-980. https://doi.org/10.1021/ol005630k
27. Linli He,, Meni Wanunu,, Hoe-Sup Byun, and, Robert Bittman. Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction. The Journal of Organic Chemistry 1999, 64 (16) , 6049-6055. https://doi.org/10.1021/jo9906375
28. Guigen Li,, Han-Xun Wei,, Sun Hee Kim, and, Margret Neighbors. Transition Metal-Catalyzed Regioselective and Stereoselective Aminochlorination of Cinnamic Esters. Organic Letters 1999, 1 (3) , 395-398. https://doi.org/10.1021/ol990059e
29. Barry M. Trost,, Curt D. Haffner,, David J. Jebaratnam,, Michael J. Krische, and, Andrew P. Thomas. The Palladium-Catalyzed Enyne Cycloisomerization Reaction in a General Approach to the Asymmetric Syntheses of the Picrotoxane Sesquiterpenes. Part I. First-Generation Total Synthesis of Corianin and Formal Syntheses of Picrotoxinin and Picrotin. Journal of the American Chemical Society 1999, 121 (26) , 6183-6192. https://doi.org/10.1021/ja9901821
30. Linli He,, Hoe-Sup Byun, and, Robert Bittman. A New Synthetic Route to Chiral Glycerolipid Precursors Using a Cyclic Sulfate Synthon:  Preparation of 1-O-Hexadecyl-3-O-(4‘-methoxyphenyl)- sn-glycerol and Its 1-Thio and 1-Aza Analogues. The Journal of Organic Chemistry 1998, 63 (16) , 5696-5699. https://doi.org/10.1021/jo980471s
31. Michael E. Jung,, Bruce T. Fahr, and, Derin C. D'Amico. Total Syntheses of the Cytotoxic Marine Natural Product, Aplysiapyranoid C1. The Journal of Organic Chemistry 1998, 63 (9) , 2982-2987. https://doi.org/10.1021/jo972228j
32. K. Laxma Reddy and, K. Barry Sharpless. From Styrenes to Enantiopure α-Arylglycines in Two Steps. Journal of the American Chemical Society 1998, 120 (6) , 1207-1217. https://doi.org/10.1021/ja9728177
33. Anne Cauvel,, Gilbert Renard, and, Daniel Brunel. Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups. The Journal of Organic Chemistry 1997, 62 (3) , 749-751. https://doi.org/10.1021/jo9614001
34. Giuliana Righi and, Giovanna Rumboldt, , Carlo Bonini. Stereoselective Preparation of Syn α-Hydroxy-β-amino Ester Units via Regioselective Opening of α,β-Epoxy Esters:  Enantioselective Synthesis of Taxol C-13 Side Chain and Cyclohexylnorstatine. The Journal of Organic Chemistry 1996, 61 (10) , 3557-3560. https://doi.org/10.1021/jo951441h
35. Hongqing Yao, Chuan Wang. Yttrium-Catalyzed Regioselective Aminolysis of 2,3-Epoxy Esters and Amides. Synlett 2023, 34 (20) , 2471-2475. https://doi.org/10.1055/a-2077-5084
36. Shijie Xu, Fan Yang, Hui Fan, Xuechun Zhao, Yao Xu, Shuo Wang, Xiaoxiang Zhang. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted reduction of azides to amines under metal-free conditions. New Journal of Chemistry 2022, 46 (21) , 9994-9998. https://doi.org/10.1039/D2NJ00341D
37. Muniappan Thirumalaikumar. Ring Opening Reactions of Epoxides. A Review. Organic Preparations and Procedures International 2022, 54 (1) , 1-39. https://doi.org/10.1080/00304948.2021.1979357
38. Ryan Moreira, Michael Noden, Scott D. Taylor. Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides. Synthesis 2021, 53 (03) , 391-417. https://doi.org/10.1055/s-0040-1707314
39. Daichi Nakamura, Yusuke Sasano, Yoshiharu Iwabuchi. Ln(OTf) 3 -catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols. Organic & Biomolecular Chemistry 2019, 17 (14) , 3581-3589. https://doi.org/10.1039/C8OB02448K
40. Richard C. Larock, Shilpa A. Worlikar. Formation of Alcohols and Phenols by Ether Cleavage. 2018, 1-106. https://doi.org/10.1002/9781118662083.cot07-007
41. Maciej Malinowski, Raphaël Hensienne, Nicolas Kern, Damien Tardieu, Anne Bodlenner, Damien Hazelard, Philippe Compain. Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars. Organic & Biomolecular Chemistry 2018, 16 (25) , 4688-4700. https://doi.org/10.1039/C8OB01065J
42. Richard C. Larock, Tuanli Yao. Formation of Nitriles, Carboxylic Acids, and Derivatives by Oxidation, Substitution, and Addition. 2017, 1-85. https://doi.org/10.1002/9781118662083.cot09-001
43. Fabiola I. López, Fabiola N. de la Cruz, Julio López, J. Merced Martínez, Yolanda Alcaraz, Francisco Delgado, Amanda Sánchez-Recillas, Samuel Estrada-Soto, Miguel A. Vázquez. A simple method for the synthesis of 1,3-diaminopropan-2-ols derivatives and their ex vivo relaxant activity on isolated rat tracheal rings. Medicinal Chemistry Research 2017, 26 (6) , 1325-1335. https://doi.org/10.1007/s00044-017-1853-6
44. Marcin Ufnal, Anna Zadlo, Ryszard Ostaszewski. TMAO: A small molecule of great expectations. Nutrition 2015, 31 (11-12) , 1317-1323. https://doi.org/10.1016/j.nut.2015.05.006
45. . Chemoselective Reaction. 2015, 205-239. https://doi.org/10.1002/9783527688166.ch8
46. Francisco Sarabia, Carlos Vivar‐García, Cristina García‐Ruiz, Antonio Sánchez‐Ruiz, María Soledad Pino‐González, Miguel García‐Castro, Samy Chammaa. Exploring the Reactivity of Chiral Glycidic Amides for Their Applications in Synthesis of Bioactive Compounds. European Journal of Organic Chemistry 2014, 2014 (18) , 3847-3867. https://doi.org/10.1002/ejoc.201402221
47. Vincenzo Piccialli. Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species. Molecules 2014, 19 (5) , 6534-6582. https://doi.org/10.3390/molecules19056534
48. S. Thurow, F. Penteado, G. Perin, R. G. Jacob, D. Alves, E. J. Lenardão. Metal and base-free synthesis of arylselanyl anilines using glycerol as a solvent. Green Chemistry 2014, 16 (8) , 3854. https://doi.org/10.1039/C4GC00874J
49. C. te Grotenhuis, L. Schoonen, F. P. J. T. Rutjes. 2.5.2 Cyanation of Epoxides. 2014https://doi.org/10.1055/sos-SD-213-00137
50. Sebastian Krüger, Tanja Gaich. Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis. Beilstein Journal of Organic Chemistry 2014, 10 , 163-193. https://doi.org/10.3762/bjoc.10.14
51. Evgeni A Larin, Valeri S Kochubei, Yuri M Atroshchenko. Regio- and stereoselective synthesis of new diaminocyclopentanols. Beilstein Journal of Organic Chemistry 2014, 10 , 2513-2520. https://doi.org/10.3762/bjoc.10.262
52. Charoensak Muangkaew, Praewpan Katrun, Patcharaphon Kanchanarugee, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Thaworn Jaipetch, Chutima Kuhakarn. PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: facile synthesis of β-acetoxysulfides. Tetrahedron 2013, 69 (42) , 8847-8856. https://doi.org/10.1016/j.tet.2013.08.018
53. Yichao Zhao, Wen Wang, Jian Li, Feng Wang, Xiufang Zheng, Hongying Yun, Weili Zhao, Xiaochun Dong. FeCl 3 /pyridine: dual-activation in opening of epoxide with carboxylic acid under solvent free condition. Tetrahedron Letters 2013, 54 (44) , 5849-5852. https://doi.org/10.1016/j.tetlet.2013.08.074
54. Jin Won Kim, Dae Won Cho, Gyoosoon Park, Sung Hong Kim, Choon Sup Ra. Efficient Ring Opening Reaction of Epoxides with Oxygen Nucleophiles Catalyzed by Quaternary Onium Salt. Bulletin of the Korean Chemical Society 2013, 34 (8) , 2286-2290. https://doi.org/10.5012/bkcs.2013.34.8.2286
55. Mohammad Navid Soltani Rad, Somayeh Behrouz. The base-free chemoselective ring opening of epoxides with carboxylic acids using [bmim]Br: a rapid entry into 1,2-diol mono-esters synthesis. Molecular Diversity 2013, 17 (1) , 9-18. https://doi.org/10.1007/s11030-012-9412-z
56. Himani Varshney, Aiman Ahmad, Abdul Rauf. Ring Opening of Epoxy Fatty Esters by Nucleophile to Form the Derivatives of Substituted β-Amino Alcohol. Food and Nutrition Sciences 2013, 04 (09) , 21-24. https://doi.org/10.4236/fns.2013.49A1004
57. A. A. Afon’kin, L. M. Kostrikin, A. E. Shumeiko, A. F. Popov, A. A. Matveev, V. N. Matvienko, A. F. Zabudkin. Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters. Russian Chemical Bulletin 2012, 61 (11) , 2149-2162. https://doi.org/10.1007/s11172-012-0302-4
58. Giuliana Righi, Roberto Antonioletti, Romina Pelagalli. A highly regioselective azidolysis of 2,3-epoxy amines: an unexpected [Ti(O-i-Pr)2(N3)2] mediated C-2 opening. Tetrahedron Letters 2012, 53 (42) , 5582-5584. https://doi.org/10.1016/j.tetlet.2012.07.074
59. Daniela Lanari, Oriana Piermatti, Ferdinando Pizzo, Luigi Vaccaro. Water as Reaction Medium in the Synthetic Processes Involving Epoxides. 2012, 209-232. https://doi.org/10.1007/978-94-007-1712-1_7
60. Najmadin Azizi, Elham Batebi. Highly efficient deep eutectic solvent catalyzed ring opening of epoxides. Catalysis Science & Technology 2012, 2 (12) , 2445. https://doi.org/10.1039/c2cy20456h
61. Gangavaram V. M. Sharma, Gourishetty Srikanth, Pothula Purushotham Reddy. Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA). Organic & Biomolecular Chemistry 2012, 10 (40) , 8119. https://doi.org/10.1039/c2ob26396c
62. Simona Bonollo, Daniela Lanari, Luigi Vaccaro. Ring‐Opening of Epoxides in Water. European Journal of Organic Chemistry 2011, 2011 (14) , 2587-2598. https://doi.org/10.1002/ejoc.201001693
63. . References. 2010, 439-474. https://doi.org/10.1002/9780470689493.refs
64. Vrushali H. Jadhav, Omprakash P. Bande, Vedavati G. Puranik, Dilip D. Dhavale. Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide. Tetrahedron: Asymmetry 2010, 21 (2) , 163-170. https://doi.org/10.1016/j.tetasy.2010.01.007
65. David Yu-Kai Chen, Chih-Chung Tseng. Chemistry of the cortistatins–a novel class of anti-angiogenic agents. Organic & Biomolecular Chemistry 2010, 8 (13) , 2900. https://doi.org/10.1039/c003935g
66. William P. Griffith. The Chemistry of Ruthenium Oxidation Complexes. 2009, 1-134. https://doi.org/10.1007/978-1-4020-9378-4_1
67. William P. Griffith. Oxidation of Alcohols, Carbohydrates and Diols. 2009, 135-172. https://doi.org/10.1007/978-1-4020-9378-4_2
68. Nabil Asaad, Shaun Fillery. Mechanistic studies on the synthesis of bicalutamide. Org. Biomol. Chem. 2009, 7 (4) , 678-686. https://doi.org/10.1039/B815894K
69. Peng Gao, Peng-Fei Xu, Hongbin Zhai. Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium. Tetrahedron Letters 2008, 49 (46) , 6536-6538. https://doi.org/10.1016/j.tetlet.2008.09.004
70. Biswanath Das, Vtukuri Saidi Reddy, Maddeboina Krishnaiah, Yerra Koteswara Rao. Highly regio- and stereoselective ring-opening of epoxides and aziridines with sodium azide using ammonium-12-molybdophosphate. Journal of Molecular Catalysis A: Chemical 2007, 270 (1-2) , 89-92. https://doi.org/10.1016/j.molcata.2007.01.040
71. Shivani, Asit K. Chakraborti. Zinc perchlorate hexahydrate as a new and highly efficient catalyst for synthesis of 2-hydroxysulfides by opening of epoxide rings with thiols under solvent-free conditions: Application for synthesis of the key intermediate of diltiazem. Journal of Molecular Catalysis A: Chemical 2007, 263 (1-2) , 137-142. https://doi.org/10.1016/j.molcata.2006.08.047
72. Gabriel Tojo, Marcos Fernández. Ruthenium Tetroxide and Other Ruthenium Compounds. 2007, 61-78. https://doi.org/10.1007/0-387-35432-8_5
73. Zhenghong Zhou, Zhaoming Li, Wang Quanyong, Bing Liu, Kangying Li, Guofeng Zhao, Qilin Zhou, Chuchi Tang. (Salen)Ti(IV) complex catalyzed asymmetric ring-opening of epoxides using dithiophosphorus acid as the nucleophile. Journal of Organometallic Chemistry 2006, 691 (26) , 5790-5797. https://doi.org/10.1016/j.jorganchem.2006.09.049
74. Martin G. Banwell, Patricia García-García, Enrique Aguilar. Titanium Tetraisopropoxide. 2006https://doi.org/10.1002/047084289X.rt127.pub2
75. RAHULA JANIŠ, ANTONÍN KLÁSEK, JANA BOBÁLOVÁ. CHROMIUM (III) ACETATE HYDROXIDE – AN EFFICIENT CATALYST FOR PREPARATION OF 1‐MONOACYLGLYCEROLS BY THE GLYCIDOL–FATTY ACID REACTION. Journal of Food Lipids 2006, 13 (2) , 199-209. https://doi.org/10.1111/j.1745-4522.2006.00045.x
76. Francesco Fringuelli, Ferdinando Pizzo, Carla Vittoriani, Luigi Vaccaro. Polystyrene‐Supported 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene as an Efficient and Reusable Catalyst for the Thiolysis of 1,2‐Epoxides under Solvent‐Free Conditions. European Journal of Organic Chemistry 2006, 2006 (5) , 1231-1236. https://doi.org/10.1002/ejoc.200500791
77. Francesco Fringuelli, Ferdinando Pizzo, Simone Tortoioli, Cristiano Zuccaccia, Luigi Vaccaro. In(OTf) 3 -catalyzed thiolysis of 1,2-epoxides by arylthiols under SFC. A new approach for the synthesis of thiazolopyridinium ionic liquids. Green Chem. 2006, 8 (2) , 191-196. https://doi.org/10.1039/B514979G
78. Luca Banfi, Renata Riva. The P asserini Reaction. 2005, 1-140. https://doi.org/10.1002/0471264180.or065.01
79. Eloísa Martín‐Zamora, Ana Ferrete, José M. Llera, Jesús M. Muñoz, Rafael R. Pappalardo, Rosario Fernández, José M. Lassaletta. Studies on Stereoselective [2+2] Cycloadditions between N,N‐Dialkylhydrazones and Ketenes. Chemistry – A European Journal 2004, 10 (23) , 6111-6129. https://doi.org/10.1002/chem.200400452
80. Laura Martín-Ortiz, Samy Chammaa, María Soledad Pino-González, Antonio Sánchez-Ruiz, Miguel García-Castro, Carmen Assiego, Francisco Sarabia. Isomerization of E-α,β-epoxyamides to Z-α,β-epoxyamides and synthetic applications based on regio- and stereoselective oxirane ring openings. Tetrahedron Letters 2004, 45 (49) , 9069-9072. https://doi.org/10.1016/j.tetlet.2004.10.034
81. Hartmuth C. Kolb, K. Barry Sharpless. Asymmetric Aminohydroxylation. 2004, 309-336. https://doi.org/10.1002/9783527619405.ch5f
82. Martin Eipert, Cäcilia Maichle-Mössmer, Martin E Maier. Use of epoxidation and epoxide opening reactions for the synthesis of highly functionalized 1-oxaspiro[4.5]decan-2-ones and related compounds. Tetrahedron 2003, 59 (40) , 7949-7960. https://doi.org/10.1016/j.tet.2003.08.010
83. Seiki Saito, Kanji Komada, Toshio Moriwake. Diethyl (2S,3R)‐2‐(N‐tert‐butoxycarbonyl)amino‐ 3‐Hydroxysuccinate. 2003, 184-184. https://doi.org/10.1002/0471264180.os073.19
84. Osamu Nakagawa, Kei Shimoda, Sunsuke Izumi, Toshifumi Hirata. Asymmetric epoxidation of digeranyl by cultured cells of Nicotiana tabacum. Journal of Labelled Compounds and Radiopharmaceuticals 2003, 46 (5) , 401-409. https://doi.org/10.1002/jlcr.681
85. S. Kobayashi, Y. Mori, Y. Yamashita. Metal Complexes as Lewis-acid Catalysts in Organic Synthesis. 2003, 399-444. https://doi.org/10.1016/B0-08-043748-6/09019-8
86. F. Fringuelli, F. Pizzo, S. Tortoioli, L. Vaccaro. Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water. Green Chem. 2003, 5 (4) , 436-440. https://doi.org/10.1039/B303011C
87. Ashok M. Salunkhe, P. Veeraraghavan Ramachandran, Herbert C. Brown. Selective reductions. Part 60: Chemoselective reduction of organyl azides with dichloroborane–dimethyl sulfide. Tetrahedron 2002, 58 (50) , 10059-10064. https://doi.org/10.1016/S0040-4020(02)01322-4
88. Zhaoming Li, Zhenghong Zhou, Kangying Li, Lixin Wang, Qilin Zhou, Chuchi Tang. Regio- and stereoselective ring-opening of epoxides using organic dithiophosphorus acids as nucleophiles. Tetrahedron Letters 2002, 43 (42) , 7609-7611. https://doi.org/10.1016/S0040-4039(02)01715-X
89. Adyl Oussaid, Bernard Garrigues, Boualem Oussaid, Fatima Benyaquad. Les Sels de Bismuth (III) Comme Catalyseurs Dans la Reaction D'ouverture Des Epoxydes Par Les Amines. Phosphorus, Sulfur, and Silicon and the Related Elements 2002, 177 (10) , 2315-2320. https://doi.org/10.1080/10426500214113
90. R. Voges. From chiral bromo[ 13,14 C n ]acetyl sultams to complex molecules singly/multiply labelled with isotopic carbon. Journal of Labelled Compounds and Radiopharmaceuticals 2002, 45 (10) , 867-897. https://doi.org/10.1002/jlcr.610
91. David O Arbelo, José A Prieto. Cesium propionate as an epoxide cleavage and inversion reagent. Tetrahedron Letters 2002, 43 (22) , 4111-4114. https://doi.org/10.1016/S0040-4039(02)00739-6
92. Rosario Fernández, Ana Ferrete, José M. Lassaletta, José M. Llera, Eloísa Martín-Zamora. N,N-Dialkylhydrazones as the Imine Component in the Staudinger-Like [2+2] Cycloaddition to Benzyloxyketene. Angewandte Chemie 2002, 114 (5) , 859-861. https://doi.org/10.1002/1521-3757(20020301)114:5<859::AID-ANGE859>3.0.CO;2-K
93. Atsushi Miyata, Masakazu Murakami, Ryo Irie, Tsutomu Katsuki. Chemoselective aerobic oxidation of primary alcohols catalyzed by a ruthenium complex. Tetrahedron Letters 2001, 42 (40) , 7067-7070. https://doi.org/10.1016/S0040-4039(01)01447-2
94. Martin G. Banwell. Titanium Tetraisopropoxide. 2001https://doi.org/10.1002/047084289X.rt127
95. Francesco Fringuelli, Ferdinando Pizzo, Luigi Vaccaro. AlCl 3 as an efficient Lewis acid catalyst in water. Tetrahedron Letters 2001, 42 (6) , 1131-1133. https://doi.org/10.1016/S0040-4039(00)02164-X
96. Charles M Marson. Oxygen-Directed Carbocyclizations of Epoxides. Tetrahedron 2000, 56 (45) , 8779-8794. https://doi.org/10.1016/S0040-4020(00)00789-4
97. Hirokazu Urabe, Fumie Sato. Titanium(IV) Lewis Acids. 2000, 653-798. https://doi.org/10.1002/9783527618309.ch15
98. William P. Griffith, Abdel G. Shoair, Maria Suriaatmaja. Ruthenium-Catalysed Cleavage of Alkenes and Alkynes to Carboxylic Acids. Synthetic Communications 2000, 30 (17) , 3091-3095. https://doi.org/10.1080/00397910008086915
99. Rahula Janiš, Jiří Krejčí, Antonín Klásek. Preparation of 1-monoacyIgIyceroIs from gIycidoI and fatty acids cataIyzed by the chromium(III)-fatty acid system. European Journal of Lipid Science and Technology 2000, 102 (5) , 351-354. https://doi.org/10.1002/(SICI)1438-9312(200005)102:5<351::AID-EJLT351>3.0.CO;2-J
100. Mahavir Prashad, Yansong Lu, Hong-Yong Kim, Bin Hu, Oljan Repic, Thomas J. Blacklock. An Improved and Practical Sharpless Oxidation of Primary Alcohols to the Carboxylic Acids. Synthetic Communications 1999, 29 (17) , 2937-2942. https://doi.org/10.1080/00397919908086465