Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5347-5350

  Corey, E J ^a   Noe, Mark C ^a   Xu, Feng ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHIRALITY; PHASE TRANSITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032560703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01067-3     Document Type: Article

References (15)

1. 1. Corey, E. J.; Xu, F; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
2. 2. For the early work on the application of substrate 2 to the enantioselective synthesis of α-amino acids see (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
3. (b) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507.
4. (c) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181.
5. (d) O'Donnell, M. J. et al. U.S. Patent 5,554,753, September 10, 1996.
6. (e) O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. in Phase-Transfer Catalysis, M. E. Halpern, Ed., ACS Symposium Series 659, American Chemical Society, Washington, D.C., 1997, Chapter 10.
7. 3. (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038.
8. (b) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
9. (c) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861.
10. (d) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319.
11. (e) Corey, E. J.; Noe, M. C.; Sarshar, S. J. Am. Chem. Soc. 1993, 115, 3828.
12. 4. The 25:1 diastereoselectivity in the formation of 9 is especially noteworthy. For a review of stereoselective Michael reactions, see Rossiter, B.; Swingle, N. Chem. Rev. 1992, 92, 771.
13. 1(I>2σI) = 0.0461.
14. (b) Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
15. 6. This research was support by the National Science Foundation and the National Institutes of Health.