Abstract

Free radical hydrostannation of methyl ( 2) and (−)-menthyl ( 3) ( E)-2,3-diphenylpropenoates and ( Z)-2,3-diphenylpropenenitrile with (−)-menthyldimethyltin hydride ( 1) takes place with high diastereoselectivity. The observed 1,2-stereoinduction is explained taking into account that the combination of both allylic strain effects and the hyperconjugation existing between the β-trialkyltin substituent and the half filled carbon p orbital leads to particularly stable conformations in the intermediate radicals. These results, together with those reported earlier, indicate that it is possible to predict the stereochemistry of the hydrostannation products by considering the type of substituents attached to the olefinic bond and the preferred conformation of the intermediate radicals resulting from the addition of the organotin radical. These studies also demonstrate that it is possible to achieve asymmetric hydrostannations using organotin hydrides with chiral organic ligands. Full 1H-, 13C-, and 119Sn-NMR data of the new organotin adducts are given.

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