Allylation and Crotylation of Ketones and Aldehydes Using Potassium Organotrifluoroborate Salts under Lewis Acid and Montmorillonite K10 Catalyzed Conditions

This article is cited by 64 publications.

1. Xiu-Xia Liang, Chen Zhu, Wang Zhang, Ya-Nan Du, Lei Xu, Lihua Liu, Yicheng Zhang, Man-Yi Han. Nucleophilic Allylation of Acylsilanes in Water: An Effective Alternative to Functionalized Tertiary α-Silylalcohols. The Journal of Organic Chemistry 2023, 88 (16) , 12087-12099. https://doi.org/10.1021/acs.joc.3c00668
2. Kieran Nicholson, Yuxuan Peng, Natalia Llopis, Dominic R. Willcox, Gary S. Nichol, Thomas Langer, Alejandro Baeza, Stephen P. Thomas. Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes. ACS Catalysis 2022, 12 (17) , 10887-10893. https://doi.org/10.1021/acscatal.2c03158
3. Maja W. Chojnacka, Robert A. Batey. Total Synthesis of (+)-Prunustatin A: Utility of Organotrifluoroborate-Mediated Prenylation and Shiina MNBA Esterification and Macrolactonization To Avoid a Competing Thorpe–Ingold Effect Accelerated Transesterification. Organic Letters 2018, 20 (18) , 5671-5675. https://doi.org/10.1021/acs.orglett.8b02396
4. Colin Diner and Kálmán J. Szabó . Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis. Journal of the American Chemical Society 2017, 139 (1) , 2-14. https://doi.org/10.1021/jacs.6b10017
5. Truong N. Nguyen, Thien S. Nguyen, and Jeremy A. May . Brønsted Acid Catalyzed Homoconjugate Addition of Organotrifluoroborates to Arylated Cyclopropyl Ketones. Organic Letters 2016, 18 (15) , 3786-3789. https://doi.org/10.1021/acs.orglett.6b01795
6. Patrick B. Brady and Erick M. Carreira . Addition of Trifluoroborates to Oxetanyl N,O-Acetals: Entry into Spiro and Fused Saturated Heterocycles. Organic Letters 2015, 17 (13) , 3350-3353. https://doi.org/10.1021/acs.orglett.5b01607
7. John Janetzko and Robert A. Batey . Organoboron-Based Allylation Approach to the Total Synthesis of the Medium-Ring Dilactone (+)-Antimycin A1b. The Journal of Organic Chemistry 2014, 79 (16) , 7415-7424. https://doi.org/10.1021/jo501134d
8. Ramsay E. Beveridge and Robert A. Batey . An Organotrifluoroborate-Based Convergent Total Synthesis of the Potent Cancer Cell Growth Inhibitory Depsipeptides Kitastatin and Respirantin. Organic Letters 2014, 16 (9) , 2322-2325. https://doi.org/10.1021/ol500484f
9. Yongda Zhang, Ning Li, Navneet Goyal, Guisheng Li, Heewon Lee, Bruce Z. Lu, and Chris H. Senanayake . Solvent-Free Methallylboration of Ketones Accelerated by tert-Alcohols. The Journal of Organic Chemistry 2013, 78 (11) , 5775-5781. https://doi.org/10.1021/jo4006574
10. Rauful Alam, Mihai, Raducan, Lars Eriksson, and Kálmán J. Szabó . Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions. Organic Letters 2013, 15 (10) , 2546-2549. https://doi.org/10.1021/ol401055m
11. Yongda Zhang, Ning Li, Bo Qu, Shengli Ma, Heewon Lee, Nina C. Gonnella, Joe Gao, Wenjie Li, Zhulin Tan, Jonathan T. Reeves, Jun Wang, Jon C. Lorenz, Guisheng Li, Diana C. Reeves, Ajith Premasiri, Nelu Grinberg, Nizar Haddad, Bruce Z. Lu, Jinhua J. Song, and Chris H. Senanayake . Asymmetric Methallylation of Ketones Catalyzed by a Highly Active Organocatalyst 3,3′-F2-BINOL. Organic Letters 2013, 15 (7) , 1710-1713. https://doi.org/10.1021/ol400498a
12. Timothy R. Ramadhar, Jazmin Bansagi, and Robert A. Batey . Mild Double Allylboration Reactions of Nitriles and Acid Anhydrides Using Potassium Allyltrifluoroborate. The Journal of Organic Chemistry 2013, 78 (3) , 1216-1221. https://doi.org/10.1021/jo302194n
13. Lauren M. Fleury, Andrew D. Kosal, James T. Masters, and Brandon L. Ashfeld . Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics. The Journal of Organic Chemistry 2013, 78 (2) , 253-269. https://doi.org/10.1021/jo301726v
14. Takeshi Takeda, Takuya Nishimura, Satoshi Yoshida, Fumiya Saiki, Yuki Tajima, and Akira Tsubouchi . Diastereoselective Addition of Allyltitanocenes to Cyclic Enones. Organic Letters 2012, 14 (8) , 2042-2045. https://doi.org/10.1021/ol300562g
15. Iris Sancho-Sanz, Delia Miguel, Alba Millán, Rosa E. Estévez, Juan L. Oller-López, Enrique Álvarez-Manzaneda, Rafael Robles, Juan M. Cuerva, and José Justicia. Titanocene(III)-Promoted Barbier-type Crotylation of Carbonyl Compounds. The Journal of Organic Chemistry 2011, 76 (2) , 732-735. https://doi.org/10.1021/jo102269d
16. 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
17. Maureen K. Reilly and Scott D. Rychnovsky. Allyl Transfer to Aldehydes and Ketones by Brønsted Acid Activation of Allyl and Crotyl 1,3,2-Dioxazaborolidines. Organic Letters 2010, 12 (21) , 4892-4895. https://doi.org/10.1021/ol1020515
18. Bishnu Dutta, Noga Gilboa and Ilan Marek. Highly Diastereoselective Preparation of Homoallylic Alcohols Containing Two Contiguous Quaternary Stereocenters in Acyclic Systems from Simple Terminal Alkynes. Journal of the American Chemical Society 2010, 132 (16) , 5588-5589. https://doi.org/10.1021/ja101371x
19. Kevin J. Gonzalez, Alexander W. Rand, Brian M. Stoltz. Development of a Non‐Directed Petasis‐Type Reaction by an Aromaticity‐Disrupting Strategy. Angewandte Chemie 2023, 135 (14) https://doi.org/10.1002/ange.202218921
20. Kevin J. Gonzalez, Alexander W. Rand, Brian M. Stoltz. Development of a Non‐Directed Petasis‐Type Reaction by an Aromaticity‐Disrupting Strategy. Angewandte Chemie International Edition 2023, 62 (14) https://doi.org/10.1002/anie.202218921
21. Preeti Oswal, Aayushi Arora, Anurag Bahuguna, Suraj Purohit, Khushi Joshi, Pankaj Sharma, Arun Kumar. Palladacycle versus coordination complex of palladium(II) with a bulky organophosphorus (P,N) ligand: Application in catalysis of allylation of aldehydes. Results in Chemistry 2023, 5 , 100683. https://doi.org/10.1016/j.rechem.2022.100683
22. Joseph M. Zanghi, Simon J. Meek. Cu‐Catalyzed Diastereo‐ and Enantioselective Reactions of γ,γ‐Disubstituted Allyldiboron Compounds with Ketones. Angewandte Chemie 2020, 132 (22) , 8529-8533. https://doi.org/10.1002/ange.202000675
23. Joseph M. Zanghi, Simon J. Meek. Cu‐Catalyzed Diastereo‐ and Enantioselective Reactions of γ,γ‐Disubstituted Allyldiboron Compounds with Ketones. Angewandte Chemie International Edition 2020, 59 (22) , 8451-8455. https://doi.org/10.1002/anie.202000675
24. Eliška Vyskočilová, Anna Gruberová, Mariya Shamzhy, Eva Vrbková, Jiří Krupka, Libor Červený. Prins cyclization in 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol preparation using smectite clay as catalyst. Reaction Kinetics, Mechanisms and Catalysis 2018, 124 (2) , 711-725. https://doi.org/10.1007/s11144-018-1371-7
25. Gilson B. da Silva, Paulo H. Menezes, Ivani Malvestiti, Eduardo H.L. Falcão, Severino Alves Jr, Jarosław Chojnacki, Fausthon F. da Silva. Copper-based 2D-coordination polymer as catalyst for allylation of aldehydes. Journal of Molecular Structure 2018, 1155 , 530-535. https://doi.org/10.1016/j.molstruc.2017.10.096
26. Pauli Wrigstedt, Vladimir Iashin, Kalle Lagerblom, Juha Keskiväli, Konstantin Chernichenko, Timo Repo. Syntheses of C-6 Aryl- and Alkynyl-Substituted Thymidines from Thymidine trans -5,6-Bromohydrins. European Journal of Organic Chemistry 2017, 2017 (4) , 880-891. https://doi.org/10.1002/ejoc.201601219
27. Viviane de Souza, Cristiane Oliveira, Thiago de Souza, Paulo Menezes, Severino Alves, Ricardo Longo, Ivani Malvestiti. A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst. Molecules 2016, 21 (11) , 1539. https://doi.org/10.3390/molecules21111539
28. Nelli Elizarov, Mathieu Pucheault, Sylvain Antoniotti. Highly Efficient Hosomi-Sakurai Reaction of Aromatic Aldehydes Catalyzed by Montmorillonite Doped with Simple Bismuth(III) Salts. Batch and Continuous Flow Studies.. ChemistrySelect 2016, 1 (12) , 3219-3222. https://doi.org/10.1002/slct.201600916
29. Takeo Nakano, Kohei Endo, Yutaka Ukaji. Silver-Catalyzed Allylation of Ketones and Intramolecular Cyclization through Carbene Intermediates from Cyclopropenes Under Ambient Conditions. Chemistry - An Asian Journal 2016, 11 (5) , 713-721. https://doi.org/10.1002/asia.201501196
30. Jucleiton J.R. Freitas, Tulio R. Couto, Italo H. Cavalcanti, Juliano C.R. Freitas, Queila P.S. Barbosa, Roberta A. Oliveira. Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil. Tetrahedron Letters 2016, 57 (7) , 760-765. https://doi.org/10.1016/j.tetlet.2016.01.017
31. Sudipta Raha Roy, Dorian Didier, Amir Kleiner, Ilan Marek. Diastereodivergent combined carbometalation/zinc homologation/C–C fragmentation reaction as an efficient tool to prepare acyclic allylic quaternary carbon stereocenters. Chemical Science 2016, 7 (9) , 5989-5994. https://doi.org/10.1039/C6SC02191C
32. Jiun-Le Shih, Thien S. Nguyen, Jeremy A. May. Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D. Angewandte Chemie 2015, 127 (34) , 10069-10073. https://doi.org/10.1002/ange.201503528
33. Jiun‐Le Shih, Thien S. Nguyen, Jeremy A. May. Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D. Angewandte Chemie International Edition 2015, 54 (34) , 9931-9935. https://doi.org/10.1002/anie.201503528
34. Jack L.-Y. Chen, Varinder K. Aggarwal. Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines Using Borinic Esters: Contiguous Quaternary Stereogenic Centers. Angewandte Chemie 2014, 126 (41) , 11172-11176. https://doi.org/10.1002/ange.201407127
35. Jack L.-Y. Chen, Varinder K. Aggarwal. Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines Using Borinic Esters: Contiguous Quaternary Stereogenic Centers. Angewandte Chemie International Edition 2014, 53 (41) , 10992-10996. https://doi.org/10.1002/anie.201407127
36. Jomy Joseph, Florian Jaroschik, Dominique Harakat, K. V. Radhakrishnan, Jean-Luc Vasse, Jan Szymoniak. Titanium-Catalyzed Hydroalumination of Conjugated Dienes: Access to Fulvene-Derived Allylaluminium Reagents and Their Diastereoselective Reactions with Carbonyl Compounds. Chemistry - A European Journal 2014, 20 (18) , 5433-5438. https://doi.org/10.1002/chem.201304775
37. P.V. Ramachandran, P.D. Gagare, D.R. Nicponski. 2.01 Allylborons. 2014, 1-71. https://doi.org/10.1016/B978-0-08-097742-3.00201-9
38. Prashant B. Thorat, Santosh V. Goswami, Sudhakar R. Bhusare. An efficient route for the allylation of arylaldehydes to give enantiopure homoallylic alcohols. Tetrahedron: Asymmetry 2013, 24 (20) , 1324-1330. https://doi.org/10.1016/j.tetasy.2013.08.016
39. Túlio R. Couto, Juliano C.R. Freitas, Italo H. Cavalcanti, Roberta A. Oliveira, Paulo H. Menezes. Allylation of aldehydes with potassium allyltrifluoroborate catalyzed by Amberlyst A-15. Tetrahedron 2013, 69 (34) , 7006-7010. https://doi.org/10.1016/j.tet.2013.06.050
40. Juliano C.R. Freitas, Cristiane K. de Oliveira, Edilanio C. Cunha, Ivani Malvestiti, Severino Alves, Ricardo L. Longo, Paulo H. Menezes. Allylation of aldehydes with potassium allyltrifluoroborate catalyzed by lanthanide-based metal-organic framework. Tetrahedron Letters 2013, 54 (12) , 1558-1561. https://doi.org/10.1016/j.tetlet.2013.01.035
41. Farhad Nowrouzi, Robert A. Batey. Regio- and Stereoselective Allylation and Crotylation of Indoles at C2 Through the Use of Potassium Organotrifluoroborate Salts. Angewandte Chemie 2013, 125 (3) , 926-929. https://doi.org/10.1002/ange.201207978
42. Farhad Nowrouzi, Robert A. Batey. Regio- and Stereoselective Allylation and Crotylation of Indoles at C2 Through the Use of Potassium Organotrifluoroborate Salts. Angewandte Chemie International Edition 2013, 52 (3) , 892-895. https://doi.org/10.1002/anie.201207978
43. Ruth López-Durán, Alicia Martos-Redruejo, Elena Buñuel, Virtudes Pardo-Rodríguez, Diego J. Cárdenas. Preparation of allylboronates by Pd-catalysed borylative cyclisation of dienynes. Chemical Communications 2013, 49 (91) , 10691. https://doi.org/10.1039/c3cc45879b
44. Takeshi Takeda, Yasutaka Yatsumonji, Akira Tsubouchi. Highly Stereoselective Construction of Acyclic Systems by the Reaction of Allyl and Allenyltitanocenes with Ketones. Journal of Synthetic Organic Chemistry, Japan 2013, 71 (2) , 98-108. https://doi.org/10.5059/yukigoseikyokaishi.71.98
45. Alastair J. J. Lennox. General Introduction. 2013, 1-9. https://doi.org/10.1007/978-3-319-01134-9_1
46. Mihai Raducan, Rauful Alam, Kálmán J. Szabó. Palladium-Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones. Angewandte Chemie 2012, 124 (52) , 13227-13230. https://doi.org/10.1002/ange.201207951
47. Mihai Raducan, Rauful Alam, Kálmán J. Szabó. Palladium-Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones. Angewandte Chemie International Edition 2012, 51 (52) , 13050-13053. https://doi.org/10.1002/anie.201207951
48. Juliano C.R. Freitas, Túlio R. Couto, Antônio A.S. Paulino, João R. de Freitas Filho, Ivani Malvestiti, Roberta A. Oliveira, Paulo H. Menezes. Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions. Tetrahedron 2012, 68 (51) , 10611-10620. https://doi.org/10.1016/j.tet.2012.09.073
49. Fernanda Barbosa, Juliano Freitas, Caio Melo, Paulo Menezes, Roberta Oliveira. Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media. Molecules 2012, 17 (12) , 14099-14110. https://doi.org/10.3390/molecules171214099
50. Juliano C.R. Freitas, Túlio R. Couto, Antônio A.S. Paulino, João R. de Freitas Filho, Ivani Malvestiti, Roberta A. Oliveira, Paulo H. Menezes. Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions. Tetrahedron 2012, 68 (41) , 8645-8654. https://doi.org/10.1016/j.tet.2012.07.070
51. Takeshi Takeda, Masanori Yamamoto, Satoshi Yoshida, Akira Tsubouchi. Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones. Angewandte Chemie 2012, 124 (29) , 7375-7378. https://doi.org/10.1002/ange.201202808
52. Takeshi Takeda, Masanori Yamamoto, Satoshi Yoshida, Akira Tsubouchi. Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones. Angewandte Chemie International Edition 2012, 51 (29) , 7263-7266. https://doi.org/10.1002/anie.201202808
53. Tom Mejuch, Bishnu Dutta, Mark Botoshansky, Ilan Marek. Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system. Organic & Biomolecular Chemistry 2012, 10 (30) , 5803. https://doi.org/10.1039/c2ob25121c
54. Gopalpur Nagendrappa. Organic synthesis using clay and clay-supported catalysts. Applied Clay Science 2011, 53 (2) , 106-138. https://doi.org/10.1016/j.clay.2010.09.016
55. Takeshi Takeda, Hideki Wasa, Akira Tsubouchi. Regio- and stereoselective preparation of highly substituted tertiary homoallylic alcohols. Tetrahedron Letters 2011, 52 (35) , 4575-4578. https://doi.org/10.1016/j.tetlet.2011.06.111
56. Catherine L. Moody, David S. Pugh, Richard J.K. Taylor. A one-pot oxidation/allylation/oxidation sequence for the preparation of β,γ-unsaturated ketones directly from primary alcohols. Tetrahedron Letters 2011, 52 (19) , 2511-2514. https://doi.org/10.1016/j.tetlet.2011.03.033
57. Suguru Ito, Akira Hayashi, Hirotomo Komai, Hitoshi Yamaguchi, Yoshihiro Kubota, Masatoshi Asami. Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals. Tetrahedron 2011, 67 (11) , 2081-2089. https://doi.org/10.1016/j.tet.2011.01.055
58. Hiroyuki Nakamura, Kazuki Shimizu. Catalytic reactions of bis-π-allylpalladium generated from allyltrifluoroborate. Tetrahedron Letters 2011, 52 (3) , 426-429. https://doi.org/10.1016/j.tetlet.2010.11.082
59. Abel Ros, Antonio Bermejo, Varinder K. Aggarwal. Benzylic Boron Reagents Behaving as Allylic Boron Reagents towards Aldehydes: A New Asymmetric Reaction Leading to Homoallylic Alcohols with Concomitant Dearomatisation. Chemistry – A European Journal 2010, 16 (32) , 9741-9745. https://doi.org/10.1002/chem.201001174
60. Bo Wang, Jing He, Run Cang Sun. Carbamate synthesis from amines and dialkyl carbonate over inexpensive and clean acidic catalyst—Sulfamic acid. Chinese Chemical Letters 2010, 21 (7) , 794-797. https://doi.org/10.1016/j.cclet.2010.03.012
61. Matthias Theurer, Peter Fischer, Angelika Baro, Giang Son Nguyen, Robert Kourist, Uwe Bornscheuer, Sabine Laschat. Formation of chiral tertiary homoallylic alcohols via Evans aldol reaction or enzymatic resolution and their influence on the Sharpless asymmetric dihydroxylation. Tetrahedron 2010, 66 (21) , 3814-3823. https://doi.org/10.1016/j.tet.2010.03.048
62. Tao Wang, Rui-da Ma, Liu Liu, Zhuang-ping Zhan. Solvent-free solid acid-catalyzed nucleophilic substitution of propargylic alcohols: a green approach for the synthesis of 1,4-diynes. Green Chemistry 2010, 12 (9) , 1576. https://doi.org/10.1039/c0gc00117a
63. Farhad Nowrouzi, Avinash N. Thadani, Robert A. Batey. ChemInform Abstract: Allylation and Crotylation of Ketones and Aldehydes Using Potassium Organotrifluoroborate Salts under Lewis Acid and Montmorillonite K10 Catalyzed Conditions.. ChemInform 2009, 40 (46) https://doi.org/10.1002/chin.200946068
64. Olov A. Wallner, Kálmán J. Szabó, Ramsay E. Beveridge, Robert A. Batey. Potassium Trifluoro-2-propenylborate. , 1-10. https://doi.org/10.1002/047084289X.rn00710.pub2