Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

Chemical Communications

Volumn 47, Issue 13, 2011, Pages 3897-3899

  Zhang, Yan ^a   Wee Kee, Choon ^a   Lee, Richmond ^b   Fu, Xiao ^a   Ying Teck Soh, Julian ^a   Foong Loh, Esther Mun ^a   Huang, Kuo Wei ^b   Tan, Choon Hong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BRONSTED BASE; DITHIOCARBAMIC ACID; GUANIDINE; NUCLEOPHILE; THIOL;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; RING OPENING;

EID: 79952640759     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c0cc05840h     Document Type: Article

References (34)

1. D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599
2. A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim, 2006
3. X. E. Hu, Tetrahedron, 2004, 60, 2701
4. Z. Li, M. Fernández, E. N. Jacobsen, Org. Lett., 1999, 1, 1611
5. T. Mita, I. Fujimori, R. Wada, J. Wen, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2005, 127, 11252
6. K. Arai, S. Lucarini, M. M. Salter, K. Ohta, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc., 2007, 129, 8103
7. B. Wu, J. C. Gallucci, J. R. Parquette, T. V. RajanBabu, Angew. Chem., Int. Ed., 2009, 48, 1126
8. C. Schneider, Angew. Chem., Int. Ed., 2009, 48, 2082
9. E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc., 2007, 129, 12084
10. G. Della Sala, A. Lattanzi, Org. Lett., 2009, 11, 3330
11. S. E. Larson, J. C. Baso, G. Li, J. C. Antilla, Org. Lett., 2009, 11, 5186
12. Z.-B. Luo, X.-L. Hou, L.-X. Dai, Tetrahedron: Asymmetry, 2007, 18, 443
13. Z. Wang, X. Sun, S. Ye, W. Wang, B. Wang, J. Wu, Tetrahedron: Asymmetry, 2008, 19, 964
14. A. Lattanzi, G. D. Sala, Eur. J. Org. Chem., 2009, 1845
15. D. Leow, C.-H. Tan, Chem. –Asian J., 2009, 4, 488
16. Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wang, C.-H. Tan, Angew. Chem., Int. Ed., 2009, 48, 3627
17. X. Fu, W.-T. Loh, Y. Zhang, T. Chen, T. Ma, H. Liu, J. Wang, C.-H. Tan, Angew. Chem., Int. Ed., 2009, 48, 7387
18. H. Liu, D. Leow, K.-W. Huang, C.-H. Tan, J. Am. Chem. Soc., 2009, 131, 7212
19. S. Lin, D. Leow, K.-W. Huang, C.-H. Tan, Chem. –Asian J., 2009, 4, 1741
20. Y. Pan, Y. Zhao, T. Ma, Y. Yang, H. Liu, Z. Jiang, C.-H. Tan, Chem. –Eur. J., 2010, 16, 779
21. D. Leow, C.-H. Tan, Synlett, 2010, 1589
22. Z. Yu, X. Liu, L. Zhou, L. Lin, X. Feng, Angew. Chem., Int. Ed., 2009, 48, 5195
23. H. Ube, M. Shimada, M. Terada, Angew. Chem., Int. Ed., 2010, 49, 1858
24. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc., 2010, 132, 6286
25. S. Dong, X. Liu, X. Chen, F. Mei, Y. Zhang, B. Gao, L. Lin, X. Feng, J. Am. Chem. Soc., 2010, 132, 10650
26. M. J. Frisch, et al., Gaussian 09, revision A.02, Gaussian, Inc., Wallingford, CT, 2009
27. Discovery Studio, version 2.5.5.9350, Accelrys, San Diego, CA, 2009
28. A. Bondi, J. Phys. Chem., 1964, 68, 441
29. L. Antolini, M. Bucciarelli, E. Caselli, P. Davolli, A. Forni, I. Moretti, F. Prati, G. Torre, J. Org. Chem., 1997, 62, 8784
30. S. K. Kumar, L. Kumar, V. L. Sharma, A. Jain, R. K. Jain, J. P. Maikhuri, M. Kumar, P. K. Shukla, G. Gupta, Eur. J. Med. Chem., 2008, 43, 2247
31. M. Karikomi, T. Yamazaki, T. Toda, Chem. Lett., 1993, 1965
32. A. Ziyaei-Haimjani, M. R. Saidi, Can. J. Chem., 2006, 84, 1515
33. B. C. Ranu, A. Saha, S. Banerjee, Eur. J. Org. Chem., 2008, 519
34. V. Kesavan, B.-D. Danièle, J.-P. Bgéué, Tetrahedron Lett., 2000, 41, 2895