Enantioselective Synthesis of L-CCG-I

Subhash P Chavan; Pallavi Sharma; Rasapalli Sivappa; Mohan M Bhadbhade; Rajesh G Gonnade; Uttam R Kalkote

doi:10.1021/jo0345188

Enantioselective Synthesis of L-CCG-I

J Org Chem. 2003 Aug 22;68(17):6817-9. doi: 10.1021/jo0345188.

Authors

Subhash P Chavan¹, Pallavi Sharma, Rasapalli Sivappa, Mohan M Bhadbhade, Rajesh G Gonnade, Uttam R Kalkote

Affiliation

¹ Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune 411008, India. spchavan@dalton.ncl.res.in

PMID: 12919057
DOI: 10.1021/jo0345188

Abstract

Introduction of natural menthol as the chiral auxiliary in a gamma-Br-alpha,beta-unsaturated ester leads to enantioselective generation of three chiral centers in a single step on reaction with a glycine anion equivalent to provide L-CCG-I in 94% ee.

Publication types

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

MeSH terms

Amino Acids, Dicarboxylic / chemical synthesis*
Amino Acids, Dicarboxylic / chemistry
Glycine / analogs & derivatives*
Glycine / chemical synthesis*
Glycine / chemistry
Indicators and Reagents
Isomerism
Models, Molecular
Molecular Conformation

Substances

Amino Acids, Dicarboxylic
Indicators and Reagents
(alpha-carboxycyclopropyl)glycine
Glycine