Two-component chiral phase transfer catalysts: Enantioselective esterification of an N-acylated amino acid

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1821-1823

  Pirkle, William H ^a   Snyder, Seth Elliot ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID;

ACYLATION; ARTICLE; CATALYSIS; CHEMISTRY; ESTERIFICATION; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY;

ACYLATION; AMINO ACIDS; CATALYSIS; CHROMATOGRAPHY, LIQUID; ESTERIFICATION;

EID: 0035859319     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015823n     Document Type: Article

References (10)

1. O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 1993; pp 727-756.
2. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
3. (b) Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447.
4. (c) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenwaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745-4752.
5. (a) Pirkle, W. H.; Murray, P. J. J. Chromatogr. 1993, 641, 11-19.
6. (b) Pirkle, W. H.; Koscho, M. E. J. Chromatogr. A. 1999, 840, 151-158.
7. (a) Kellner, K.-H.; Blasch, A.; Chmiel, H.; Lämmerhofer, M.; Lindner, W. Chirality 1997, 9, 268-273.
8. (b) Pirkle, W. H.; Bowen, W. E. Tetrahedron: Asymmetry 1994, 5, 773-776.
9. A preliminary account of this research was presented at the International Symposium on Chiral Discrimination, 1998; Vienna, Austria.
10. Use of stronger bases lead to subsequent enantioselective ester hydrolysis. This aspect of two-component chiral phase transfer catalysis is being actively pursued and will be reported shortly.