Journal of Organic Chemistry 2012-10-19

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

Maung Kyaw Moe Tun, Seth B Herzon

Index: J. Org. Chem. 77(20) , 9422-5, (2012)

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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).

Related Compounds

  • Pulegone
  • (S)-(-)-Pulegone

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