A general method for the enantioselective synthesis of α-chiral heterocycles

Organic Letters

Volumn 14, Issue 23, 2012, Pages 6104-6107

  Le, Phong Q ^a   Nguyen, Thien S ^a   May, Jeremy A ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CHEMISTRY, ORGANIC; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84870880980     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3030605     Document Type: Article

References (38)

1. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
2. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461
3. Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341
4. de Sa Alves, F. R.; Barreiro, E. J.; Manssour Fraga, C. A. Mini-Rev. Med. Chem. 2009, 9, 782
5. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
6. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5 th ed.; John Wiley & Sons: West Sussex, U.K., 2010.
7. Çelebi-Ölçüm, N.; Boal, B. W.; Huters, A. D.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 5752
8. Jensen, K.; Thorhauge, J.; Hazell, R.; Jorgensen, K. Angew. Chem., Int. Ed. 2001, 40, 160
9. Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172
10. Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C. Org. Lett. 2007, 9, 2609
11. Lee, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 15438
12. Viswanathan, R.; Smith, C. R.; Prabhakaran, E. N.; Johnston, J. N. J. Org. Chem. 2008, 73, 3040
13. Ganesh, M.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 16464
14. Zheng, W.; Zhang, Z.; Kaplan, M. J.; Antilla, J. C. J. Am. Chem. Soc. 2011, 133, 3339
15. Lundy, B. J.; Jansone-Popova, S.; May, J. A. Org. Lett. 2011, 13, 4958
16. Brown, C.; Chong, J.; Shen, L. Tetrahedron 1999, 55, 14233
17. Chong, J. M.; Shen, L.; Taylor, N. J. J. Am. Chem. Soc. 2000, 122, 1822
18. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2005, 127, 3244
19. Wu, T. R.; Chong, J. M. Org. Lett. 2006, 8, 15
20. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2006, 128, 9646
21. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2007, 129, 4908
22. Turner, H. M.; Patel, J.; Niljianskul, N.; Chong, J. M. Org. Lett. 2011, 13, 5796
23. Pellegrinet, S. C.; Goodman, J. M. J. Am. Chem. Soc. 2006, 128, 3116
24. Paton, R. S.; Goodman, J. M.; Pellegrinet, S. C. J. Org. Chem. 2008, 73, 5078
25. Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660
26. Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2007, 129, 15398
27. Lou, S.; Schaus, S. E. J. Am. Chem. Soc. 2008, 130, 6922
28. Bishop, J. A.; Lou, S.; Schaus, S. E. Angew. Chem., Int. Ed. 2009, 48, 4337
29. Barnett, D. S.; Schaus, S. E. Org. Lett. 2011, 13, 4020
30. In the case of ketone and aldehyde allylations, catalyst release appears to be rate determining: Barnett, D. S.; Moquist, P. N.; Schaus, S. E. Angew. Chem., Int. Ed. 2009, 48, 8679
31. Sheppard, W. A. J. Am. Chem. Soc. 1970, 92, 5419
32. Makida, Y.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2012, 51, 4122
33. Yoshida, M.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 11896
34. Muraoka, O.; Sawada, T.; Morimoto, E.; Tanabe, G. Chem. Pharm. Bull. 1993, 41, 772
35. Skytte, D. M.; Nielsen, S. F.; Chen, M.; Zhai, L.; Olsen, C. E.; Christensen, S. B. J. Med. Chem. 2006, 49, 436
36. Nishikata, T.; Yamamoto, Y.; Miyaura, N. Adv. Synth. Catal. 2007, 349, 1759
37. Kobayashi, K.; Nishikata, T.; Yamamoto, Y.; Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1019
38. Frost, C.; Edwards, H.; Penrose, S.; Gleave, R. Synthesis 2010, 3243