Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one

Maung Kyaw Moe Tun; Seth B Herzon

doi:10.1021/jo3017956

Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one

J Org Chem. 2012 Oct 19;77(20):9422-5. doi: 10.1021/jo3017956. Epub 2012 Oct 3.

Authors

Maung Kyaw Moe Tun¹, Seth B Herzon

Affiliation

¹ Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

PMID: 23030397
DOI: 10.1021/jo3017956

Abstract

A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access multigram quantities of (R)-(+)-4-methylcyclohex-2-ene-1-one (1).

Publication types

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

MeSH terms

Cyclohexane Monoterpenes
Cyclohexanones / chemical synthesis*
Cyclohexanones / chemistry
Molecular Structure
Monoterpenes / chemistry*
Stereoisomerism

Substances

Cyclohexane Monoterpenes
Cyclohexanones
Monoterpenes
pulegone