The Enantioselective Synthesis of anti-β-Hydroxy-α-Amino Acids via the Reaction of Lithium Enolates of Glycine Bearing an Oxazolidine Chiral Auxiliary with Aldehydes

Edwin J. Iwanowicz; Peter Blomgren; Peter T. W. Cheng; Kennith Smith; Wan F. Lau; Yolanda Y. Pan; Henry H. Gu; Mary F. Malley; Jack Z. Gougoutas

doi:10.1055/s-1998-1736

Synlett 1998; 1998(6): 664-666
DOI: 10.1055/s-1998-1736

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The Enantioselective Synthesis of anti-β-Hydroxy-α-Amino Acids via the Reaction of Lithium Enolates of Glycine Bearing an Oxazolidine Chiral Auxiliary with Aldehydes

Edwin J. Iwanowicz^* , Peter Blomgren, Peter T. W. Cheng, Kennith Smith, Wan F. Lau, Yolanda Y. Pan, Henry H. Gu, Mary F. Malley, Jack Z. Gougoutas

^*Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, NJ 08543-4000, USA; Fax +(609)2 52 66 01; E-mail: iwanowicz@bms.com

Abstract

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A new anti-selective aldol reaction utilizing 2,4-disubstituted oxazolidine functionalized-glycine ester 1 is described. The corresponding lithium enolate of 1, has been demonstrated to undergo a highly anti-diastereoselective aldol reaction with a variety of aldehydes. Facile removal of the chiral auxiliary allows for the efficient preparation of chiral β-hydroxy-α-amino acids of erythro stereochemistry.

Aldol reaction - anti-selective amino acids - β-Hydroxy-α-Amino Acids

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