Diastereoselective Allylation of Imines with γ-Silyloxyallylstannanes Promoted by Trimethylsilyl Triflate and Application to the Synthesis of Erythro-Sphingosine

Addition of γ-silyloxyallylstannanes to imines in the presence of trimethylsilyl triflate was studied. Allylation of α-imino ester with (Z)-allylstannane proceeded to give anti-adduct as a major product, which was transformed into N,O,O-triacetyl erythro-sphingposine via appropriate functional group transformations.