Molecules (Mar 2000)

Stereoselective Synthesis of 8-Trialkylstannylmenthols

  • Julio C. Podestá,
  • Verónica Dodero,
  • Nelda N. Giagante,
  • Sandra D. Mandolesi

DOI
https://doi.org/10.3390/50300594
Journal volume & issue
Vol. 5, no. 3
pp. 594 – 595

Abstract

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Trialkyltin menthones of type 2 are obtained selectively by 1,4-addition of trialkylstannyl lithium to (-)-pulegone. Reduction of 2 with borane in THF using as catalyst the reagent prepared from borane and (S)-valinol gave a mixture of the corresponding trialkyltin alcohols 3 (Me: 84%; n-Bu: 90,6%) and 4 (Me: 16% and n-Bu: 9,4%).

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