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Deracemization of α-substituted arylacetic acids

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
7
Issue
4
Identifiers
DOI: 10.1016/0957-4166(96)00129-2

Abstract

Abstract Reaction of rac- α-substituted arylacetyl chlorides with ( R)- and ( S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone under standard esterification conditions, gave esters ( 3R,α R)- and ( 3S,α S)- 3 , respectively, with a diastereoselectivity which diminishes on increasing the steric effect of the α-substituent. Controlled acidic hydrolysis of esters 3 afforded the corresponding acids 4 with minimal racemization. Boron tribromide demethylation of (R)- and (S)-4 d gave without racemization the hydroxyacids (R)- and (S)-4 e , known precursors of ( R)- and ( S)-iodoalphionic acid.

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