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

M.      Shimizu; H.      Ando; Y.      Niwa

doi:10.2174/1570178054640688

Abstract

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.

Keywords: silyloxyallylstannane, imines, allylation, erythro-sphingosine

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Letters in Organic Chemistry

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

Volume: 2 Issue: 6

Author(s): M. Shimizu, H. Ando and Y. Niwa

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Keywords: silyloxyallylstannane, imines, allylation, erythro-sphingosine

Abstract: 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.

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Shimizu M., Ando H. and Niwa Y., Diastereoselective Allylation of Imines with γ-Silyloxyallylstannanes Promoted by Trimethylsilyl Triflate and Application to the Synthesis of Erythro-Sphingosine, Letters in Organic Chemistry 2005; 2 (6) . https://dx.doi.org/10.2174/1570178054640688