Diastereoselective Addition of Silyl Enol Ether to Chiral Imines and 1,3-Oxazolidines Using a Lewis Acid

Kimio Higashiyama; Hideyoshi Kyo; Hiroshi Takahashi

doi:10.1055/s-1998-1718

Synlett 1998; 1998(5): 489-490
DOI: 10.1055/s-1998-1718

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Diastereoselective Addition of Silyl Enol Ether to Chiral Imines and 1,3-Oxazolidines Using a Lewis Acid

Kimio Higashiyama^* , Hideyoshi Kyo, Hiroshi Takahashi

^*Institute of Medicinal Chemistry, Hoshi University, Ebara-2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan; Fax 5498-5798; E-mail: kimio@hoshi.ac.jp

Abstract

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The Lewis acid promoted reaction of silyl enol ether to chiral imines and 1,3-oxazolidines derived from (R)-phenylglycinol afforded with good diastereoselectivity the (R,R)-β-amino ester derivatives from the imines, and the (R,S)-β-amino ester derivatives from the 1,3-oxazolidines.

diastereoselective addition reaction - silyl enol ether - Lewis acid - chiral imine - chiral 1,3-oxazolidine - (R)-phenylglycinol - β-amino ester

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