Highly Diastereoselective Simmons-Smith Cyclopropanation of Allylic Amines

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4417-4420

  Aggarwal, Varinder K ^a   Fang, Guang Yu ^a   Meek, Graham ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b Chirotech Technology Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE;

ARTICLE; CHELATION; DIASTEREOISOMER; GEOMETRY; SIMMONS SMITH REACTION; STEREOCHEMISTRY;

EID: 0344065681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035713b     Document Type: Article

References (25)

1. (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323.
2. (b) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256.
3. For a review on Simmons-Smith cyclopropanation, see: Charette, A.; Beauchemin, A. Org. React. 2001, 58, 1.
4. (a) Sugimura, T.; Yoshikawa, M.; Futagawa, T.; Tai, A. Tetrahedron 1990, 46, 5955.
5. (b) Charette, A. B.; Côté, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166.
6. (c) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157.
7. (a) Kaye, P. T.; Molema, W. E. Chem. Commun. 1998, 2479.
8. (b) Arai, I.; Mori, A.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 8254.
9. Mash, E. A.; Hemperly, S. B.; Nelson, K. A.; Heidt, P. C.; Deusen, S. V. J. Org. Chem. 1990, 55, 2045.
10. Tanaka, K.; Uno, H.; Osuga, H.; Suzuki, H. Tetrahedron: Asymmetry 1994, 5, 1175
11. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986.
12. Although a single example of the cyclopropanation of an allylic amine was reported, no details were provided. See: Perraud, R.; Arnaud, P. Bull. Soc. Chim. Fr. 1968, 1540.
13. (a) Kuehne, M. E.; DiVincenzo, G. J. Org. Chem. 1972, 37, 1023.
14. (b) Kuehne, M. E.; King, J. C. J. Org. Chem. 1973, 38, 304.
15. (a) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761.
16. (b) Russ, P.; Ezzitouni, A.; Marquez, V. E. Tetrahedron Lett. 1997, 38, 723.
17. (c) Ezzitouni, A.; Russ, P.; Marquez, V. E. J. Org. Chem. 1997, 62, 4870.
18. Wittig, G.; Schwarzenbach, K. Liebigs Ann. Chem. 1961, 650, 1.
19. Aggarwal, V. K.; Fang, G. Y.; Charmant, J. P. H.; Meek, G. Org. Lett. 2003, 5, 1757.
20. (a) Charette, A. B.; Marcoux, J.-F.; Molinaro, C.; Beauchemin, A.; Brochu, C.; Isabel, E. J. Am. Chem. Soc. 2000, 122, 4508.
21. (b) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723.
22. 1H NMR that were diagnostic for the cyclopropane unit.
23. Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
24. Garcia-Valverde, M.; Nieto, J.; Pedrosa, R.; Vicente, M. Tetrahedron 1999, 55, 2755.
25. Ylide formation of N-methyl-ephedrine is possible in the absence of neighboring allylic groups. See: Denmark, S. E.; Edwards, J. Synlett 1992, 229.