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

The Journal of organic chemistry (2012-10-04)
Maung Kyaw Moe Tun, Seth B Herzon
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).

MATERIALS
Product Number
Brand
Product Description

Supelco
(+)-Pulegone, analytical standard
Sigma-Aldrich
(R)-(+)-Pulegone, 96%
Sigma-Aldrich
(R)-(+)-Pulegone, ≥90%
Sigma-Aldrich
(S)-(−)-Pulegone, 98%
Sigma-Aldrich
(R)-(+)-Pulegone, 85%, technical grade

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