Enantioselective Rauhut-Currier reactions promoted by protected cysteine

Journal of the American Chemical Society

Volumn 129, Issue 2, 2007, Pages 256-257

  Aroyan, Carrie E ^a   Miller, Scott J ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ELIMINATION REACTION; ENANTIOSELECTIVITY; ISOMERIZATION; QUANTUM YIELD; RAUHUT CURRIER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CYCLIZATION; CYSTEINE; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 33846226531     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067139f     Document Type: Article

References (19)

1. For example, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
2. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
3. Movassaghi, M.; Jacobsen, E. N. Science 2002, 298, 1904.
4. McMurry, J.; Begley, T. The Organic Chemistry of Biological Pathways; Roberts and Co.: New York, 2005.
5. Rauhut, M. M.; Currier, H. U.S. Patent 307499919630122, American Cyanamid Co., 1963.
6. (a) Wang, L.-C.; Luis, A. L.; Agapiou. K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
7. (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
8. (c) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157.
9. (d) Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737.
10. For some examples of variants with electrophilic olefins with other activating groups, see: (a) Luis, A. L.; Krische, M. J. Synthesis 2004, 15, 2579.
11. (b) Krafft, M. E.; Maxell, T. F. N. J. Am. Chem. Soc. 2005, 127, 10168.
12. For a review, see: Huddleston, R. R.; Krische, M. J. Synlett 2003, 12.
13. (a) Brown, P. M.; Käppel, N.; Murphy, P. J. Tetrahedron Lett. 2002, 43, 8707.
14. (b) Ergüden, J.-K.; Moore, H. W. Org. Lett. 1999, 1, 375.
15. For dramatic solvent effects in vinylogous Morita-Baylis-Hillman reactions, see: Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223.
16. (a) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980.
17. (b) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2005, 44, 1706.
18. (c) Raheem, I. T.; Jacobsen, E. N. Adv. Synth. Calai. 2005, 347, 1701.
19. Cho, J.-Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868.