Triethylborane Induced Selective 1,4-Reduction of α,β-Unsaturated Carbonyl Compounds with Triphenyltin Hydride or Tributyltin Hydride

Abstract

Abstract Reduction of α,β-unsaturated ketones and esters with triphenyltin hydride or tributyltin hydride in the presence of triethylborane has been studied. Whereas the reaction of α,β-unsaturated ketones (R1CH=CHCOR2) with triphenyltin hydride provided the corresponding saturated ketones (R1CH2CH2COR2), treatment of α,β-unsaturated ester (PhCH=CHCOOMe or CH3CH=CHCOO–n-C6H13) afforded an adduct (PhCH2CH(SnPh3)COOMe or CH3CH(SnPh3)CH2COO–n-C6H13).