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

V. FABRICIO TERRAZA; DARÍO C. GERBINO; JULIO C. PODESTÁ

JOURNAL OF ORGANOMETALLIC CHEMISTRY

ELSEVIER SCIENCE SA

Lugar: Amsterdam; Año: 2021 vol. 935 p. 1 - 9

0022-328X

This paper reports the synthesis of a series of (-)-menthylalkyltin dihydrides, (-)-MenRSnH2 (R =Me, n-Bu, i-Pr, t-Bu, Neophyl), starting from (-)-menthyltrimethyltin. The new (-)-menthylalkyltindihydrides 12-16 were used in a study on the stereoselective reduction of chiral (-)-menthone underdifferent reaction 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.