Helvetica chimica acta

Towards Functionalized Silicon??Containing α??Amino Acids: Asymmetric Syntheses of Sila Analogs of Homoserine and Homomethionine

RJ Smith, S Bienz

Index: Smith, Richard J.; Bienz, Stefan Helvetica Chimica Acta, 2004 , vol. 87, # 7 p. 1681 - 1696

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Citation Number: 10

Abstract

Abstract The homoserine and homomethionine sila analogs,(R)-HOSi (Me 2) CH 2 CH (NH 2) CO 2 H ((R)-21) and (R)-MeSCH 2 Si (Me 2) CH 2 CH (NH 2) CO 2 H ((R)-24), respectively, were each synthesized in nine steps and in 30 and 23% overall yield, respectively, from commercially available ClSiMe 2 CH 2 Cl. The key step of both syntheses was the asymmetric α-bromination of an Evans amide to introduce the stereogenic center ...