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

Article abstract of DOI:10.1246/bcsj.64.2585

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 (R¹CH2COR²), 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).