Synthesis of new mixed (-)-menthylalkyltin dihydrides. stereoselective reduction of chiral and prochiral ketones

Abstract

This paper reports de synthesis of a series of (-)-menthylalkyltin dihydrides, (-)-MenRSnH2 (R = Me, nBu, i-Pr, t-Bu, Neophyl), starting from (-)-menthyltrimethyltin. The new (-)-menthylalkyltin dihydrides12–16 were used in a study on the stereoselective reduction of chiral (-)-menthone under differentreaction conditions. Also the results obtained in the reductions of prochiral acetophenone (27) and 2-acetylnaphthalene (28), with (-)-menthylmethyl- (12) and (-)-menthyli-propyltin (14) dihydrides are informed. Some physical properties as well as full 1H-, 13C-, and 119Sn NMR data of the new organotin compounds are informed.