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■ (1'S,4S)-2-Aryl-4-(1'-hydroxybenzyl)-4,5-dihydrooxazole as a Useful Chiral Auxiliary for the Synthesis of β-Amino Acids and β-Lactams in a Highly Stereoselective Manner

Makoto Shimizu, Shingo Maruyama, Yasuhiro Suzuki, and Tamotsu Fujisawa*

*Department of Chemistry for Materials, Mie University, 1515 Uehama-cho, Tsu, Mie 514-5807, Japan

Abstract

(1’S,4S)-2-Aryl-4-(1’-hydroxybenzyl)-4,5-dihydrooxazole prepared from (1S,2S)-2-amino-1-phenylpropane-1,3-diol has been found to be a useful chiral auxiliary for the stereoselective synthesis of β-lactams and β-amino acids in the reaction of imine-ester enolate condensation or 1,4-addition of lithium amides to α,β-unsaturated esters.