Process for preparing enantiomerically pure alpha-amino acids

Details Process for preparing enantiomerically pure alpha-amino acids Process for preparing enantiomerically pure alpha-amino acids

1990-11-05

1992-07-21

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548208, 562401, 562575, C07D27504, C07C 2908, C07B 5300

Patent

active

051324288

ABSTRACT:
A process for enantioselectively alkylating, at the asterisked carbon atom, a single enantiomer of a glycine derivative having the general formula ZCOCH(R)NY wherein Z is a moiety derived from a chiral sultam, R is hydrogen or C.sub.1 to C.sub.10 alkyl and Y is one or more groups rendering the nitrogen atom unreactive towards alkylating agents comprises:

REFERENCES:
Oppolzer et al., Tetrahedron Letters, vol. 30, No. 44, pp. 6009-6010, 1989.
March, Advanced Organic Chemistry 3rd Ed, pp. 411-412, 1985.
Oppolzer, Tetrahedron, vol. 43, No. 18, pp. 1970-2002, 1987.
Chemical Abstracts, vol. 113, No. 3, Jul. 16, 1990, Columbus, Ohio, USA Oppolzer, W. et al. "Asymmetric alkylation of a sultam-derived glycinate equivalent: practical preparation of enantiomerically pure alpha-amino acids" p. 719, col. 1, abstract no. 24 463f. & Tetrahedron Lett. 1989, 30 (44), 6009-10.
Chemical Abstracts, vol. 108, No. 9, Feb. 29, 1988, Columbus, Ohio, USA--Seebach D. et al "Addition of chiral glycine, methionine, and vinylglycine enolate derivatives to aldehydes and Ketones in the preparation of enantiomerically pure alpha-amino-betahydroxy acids" p. 725, col. 1, abstract no. 75 788v and Helv.Chim.Acta 1987, 70(1) 239-61.

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