Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid

Alain Krief; Stephane Jeanmart; Adrian Kremer

doi:10.1021/jo8022507

Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid

J Org Chem. 2008 Dec 19;73(24):9795-7. doi: 10.1021/jo8022507.

Authors

Alain Krief¹, Stephane Jeanmart, Adrian Kremer

Affiliation

¹ Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, Namur, B-5000, Belgium. alain.krief@fundp.ac.be

PMID: 19007137
DOI: 10.1021/jo8022507

Abstract

(1R)-cis-chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.