A new catalyst for the asymmetric Henry reaction: Synthesis of β-nitroethanols in high enantiomeric excess

Organic Letters

Volumn 14, Issue 24, 2012, Pages 6270-6273

  White, James D ^a   Shaw, Subrata ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84871570717     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3030023     Document Type: Article

References (34)

1. Henry, L. C.R. Acad. Sci. Ser. C 1895, 1265
2. Henry, L. Bull. Soc. Chim. Fr. 1895, 13, 999
3. Luzzio, F. A. Tetrahedron 2001, 57, 915
4. Rosini, G.; Ballini, R. Synthesis 1988, 833
5. Sasai, H.; S-uzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418
6. Sasai, H.; Tokunga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388
7. Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem.-Eur. J. 1996, 2, 1368
8. Davis, A. V.; Driffield, M.; Smith, D. K. Org. Lett. 2001, 3, 3075
9. Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621
10. Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861
11. Risgard, T.; Gothelf, K. V.; Jorgensen, K. A. Org. Biomol. Chem. 2003, 1, 153
12. Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692
13. Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 2054
14. Zhong, Y. W.; Tian, P.; Lin, G. Q. Tetrahedron: Asymmetry 2004, 15, 771
15. Borah, J. C.; Gogoi, S.; Boruwa, J.; Kalita, B.; Barua, N. C. Tetrahedron Lett. 2004, 45, 3689
16. Zubia, A.; Cossio, F. P.; Morao, L. A.; Rieumont, M.; Lopez, X. J. Am. Chem. Soc. 2004, 126, 5243
17. Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442
18. Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881
19. Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732
20. Arai, T.; Watanabe, M.; Yanagisawa, A. Org. Lett. 2007, 9, 3595
21. Gruber-Khadjawi, M.; Purkharthofer, T.; Skranc, W.; Griengl, H. Adv. Synth. Catal. 2007, 349, 1445
22. Handa, S.; Nagawa, S.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2008, 47, 3230
23. Toussaint, A.; Pfaltz, A. Eur. J. Chem. 2008, 4591
24. Kim, H. Y.; Oh, K. Org. Lett. 2009, 11, 5682
25. Breuning, M.; Hein, D.; Steiner, M.; Gessner, V. H.; Strohmann, C. Chem.-Eur. J. 2009, 15, 12764
26. Ji, Y. Q.; Qi, G.; Judeh, Z. M. A. Eur. J. Org. Chem. 2011, 4892
27. Jin, W.; Li, X.; Wan, B. J. Org. Chem. 2011, 76, 484
28. Chougnet, A.; Zhang, G.; Liu, K.; Hausinger, D.; Kagi, A.; Allmendinger, T.; Woggon, W. D. Adv. Synth. Catal. 2011, 353, 1797
29. White, J. D.; Shaw, S. Org. Lett. 2011, 13, 2488
30. Dines, M. B.; Bird, P. H. J. Chem. Soc., Chem. Commun. 1973, 12
31. Howe, R.; Rao, B. S. J. Med. Chem. 1968, 11, 1118
32. Lunsford, C. D.; Mays, R. P.; Richman, J. A.; Murphey, R. S. J. Am. Chem. Soc. 1960, 82, 1166
33. Dukes, M.; Smith, L. H. J. Med. Chem. 1971, 14, 326
34. Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855