Ca. Vitale et Jc. Podesta, SYNTHESIS AND SOME PROPERTIES OF MIXED ALKYLDI-(-)-MENTHYLTIN HYDRIDES, Journal of the Chemical Society. Perkin transactions. I, (19), 1996, pp. 2407-2410
The synthesis and physical properties of methyldi-(-)-menthyltin 4 and
neophyldi-(-)-menthyltin 7 hydrides as well as those of their organot
in precursors are described. The reaction of hydrides 4 and 7 with car
bon tetrachloride shows that the reactivity of 4 is within the range o
f the more common triorganotin hydrides while the organotin hydride 7
reacts more slowly. A study of the reduction of acetophenone with both
hydrides shows that whereas the reduction with 4 leads to (-)-(S)-1-p
henylethanol(8.8% optical purity), the reduction with 7 affords(+)-(R)
-1-phenylethanol (6.6% optical purity); these results indicate that so
me degree of asymmetric induction can be achieved. Full H-1, C-13 and
Sn-11 NMR data are given.