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Report | Regular issue | Vol 24, No. 8, 1986, pp.2165-2167
Published online, 1st January, 1970
DOI: 10.3987/R-1986-08-2165
Asymmetric Synthesis of Cyclic Imino Acids via Chiral Shiff Bases

Jerzy Bajgrowicz, Abdelrhani El Achquar, Maris-Louise Roumestant, Chiristian Pigière, and Philippe Viallefont*

*U.S.T.L., Place E. Bataillon, 34060 Montpellier Cedex, France

Abstract

A new method of synthesis af cyclic imino acids is reported. Diastereoselective alkylation of schiff bases (derived from α-amino esters and (+) or (-) 2-hydroxypinan-3-one) with dihalogeno compounds, followed by hydrolytic cleavage and cyclisation affords the imino esters. Reactions are highly enantioselective, with one exception corresponding to steric crowding.