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Paper | Regular issue | Vol 48, No. 9, 1998, pp.1813-1823
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8211
Stereocontrolled Addition of Grignard Reagents to Chiral 1,3-Oxazolidines Having N-Methoxybenzyl Groups: Effect of N-Substituent in Diastereoselectivity

Takayasu Yamauchi, Hiroshi Takahashi, and Kimio Higashiyama*

*Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.