Tin(II)-mediated allylation. Asymmetric induction with a chiral tin(II) alkoxide

Article abstract of DOI:10.1016/0022-328X(89)80081-6

In a study of tin-mediated allylation some tin(II) species including tin(II) halides, amides, acetonates, and alkoxides, have been shown to undergo oxidation of allyl halide in the presence of benzaldehyde to give the corresponding homoallyl alcohol.The first preparation of a chiral tin(II) alkoxide, tin(II) diethyltartrate is described; its 119Sn NMR spectrum exhibits two signals at high field, consistent with a trans dimer structure.This new reagent undergoes oxidative addition of 1,3-chloroiodopropene in the presence of benzaldehyde to give an optically active phenylvinyloxirane; this represents the first enantioselective preparation of cis- and trans-vinyloxiranes from aldehydes.