Highly Enantioselective Phase‐Transfer‐Catalytic Alkylation of 2‐Phenyl‐2‐oxazoline‐4‐carboxylic Acid <i>tert</i>‐Butyl Ester for the Asymmetric Synthesis of α‐Alkyl Serines

Abstract

A facile synthesis of chiral α-alkyl serines 3 involves the asymmetric alkylation of substrates 1 with alkyl halides (RX) under phase-transfer catalysis (PTC), followed by acidic hydrolysis of the alkylation products 2. The phenyl oxazoline moiety enhances the acidity of the α proton of the ester and is an excellent protecting group for both the amino and hydroxy functions of the serine ester. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53496_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.