Tetrahedron Letters

A novel synthetic method for optically active terpenes by the ring-opening reaction of (R)-(+)-β-methyl-β-propiolactone

T Sato, T Kawara, A Nishizawa, T Fujisawa

Index: Sato, Toshio; Kawara, Tatsuo; Nishizawa, Akira; Fujisawa, Tamotsu Tetrahedron Letters, 1980 ,  vol. 21, p. 3377 - 3380

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Citation Number: 66

Abstract

Abstract Optically active terpene such as (R)-(+)-citronellol,(R)-(+)-pulegone or (S)-ar- turmerone is prepared in high enantiomeric excess from an intermediate,(R)-(+)-citronellic acid or (S)-(+)-3-p-tolylbutyric acid, which is easily prepared by the S n 2 type of ring opening reaction of (R)-(+)-β-methyl-β-propiolactone with homoprenylmagnesium bromide in the presence of a copper (I) salt or di-p-tolylcuprate.