The Journal of Organic Chemistry

Enantioselective synthesis of. alpha.-amino acid derivatives via the stereoselective alkylation of a homochiral glycine enolate synthon

JF Dellaria Jr, BD Santarsiero

Index: Dellaria, Joseph F.; Santarsiero, Bernard D. Journal of Organic Chemistry, 1989 , vol. 54, # 16 p. 3916 - 3926

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Citation Number: 125

Abstract

A new synthetic method for the enantioselective preparation of a-amino acid derivatives is presented. The key step involves the diastereoselective alkylation of the new chiral glycine enolate synthons 7 and 8 providing alkylation adducts with de of 297.6% in good yields (7340%). The reactivities of the enolates of 7 and 8 were extraordinarily sensitive to the metal counterion and solvent. Experimental conditions are described to maintain high ...