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

doi:10.1016/s0960-894x(99)00218-8

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

Bioorg Med Chem Lett. 1999 May 17;9(10):1437-42. doi: 10.1016/s0960-894x(99)00218-8.

Authors

S Hanessian¹, N Bernstein, R Y Yang, R Maguire

Affiliation

¹ Department of Chemistry, Université de Montréal, Québec, Canada.

PMID: 10360752
DOI: 10.1016/s0960-894x(99)00218-8

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alanine / analogs & derivatives*
Alanine / chemistry
Azetidinecarboxylic Acid / chemical synthesis*
Azetidinecarboxylic Acid / chemistry
Leucine / chemistry*
Molecular Structure
Phenylalanine / chemistry*

Substances

Phenylalanine
Azetidinecarboxylic Acid
1-naphthylalanine
Leucine
Alanine