Bioorganic & Medicinal Chemistry Letters 1999-05-17

Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners--conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine.

S Hanessian, N Bernstein, R Y Yang, R Maguire

Index: Bioorg. Med. Chem. Lett. 9(10) , 1437-42, (1999)

Full Text: HTML

Abstract

Enantiopure L-azetidine-2-carboxylic acid, the (3R)-phenyl, (3R)-naphthyl and (3S)-isopropyl analogs were prepared based on a zinc-mediated asymmetric addition of allylic halides to the camphor sultam derivative of glyoxylic acid O-benzyl oxime.