Tetrahedron: Asymmetry

An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids

DR Hou, SY Hung, CC Hu

Index: Hou, Duen-Ren; Hung, Shin-Yi; Hu, Chung-Cheng Tetrahedron Asymmetry, 2005 , vol. 16, # 23 p. 3858 - 3864

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Citation Number: 19

Abstract

A diastereoselective synthesis of (4R,9aR)-oxazin-1-one 4 is reported herein. Access to diastereomerically pure 4 provides the route to both (R)- and (S)-pipecolic acid using a single chiral auxiliary. In addition, both enantiomers of 2-alkyl pipecolic acids can also be prepared by alternating the sequence of alkylations. ... Chiral glycine enolate synthon, 5-phenyl morpholin-2-one 5, was prepared from the commercially available, and inexpensive, (R)-2-phenylglycinol in three ...