Stereospecific epoxide-opening reactions of 1,1-dibromo-3,4-epoxy-1-alkenes with carbon nucleophiles |
| |
| Authors: | Fumihiko Yoshimura |
| |
| Institution: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
| |
| Abstract: | The stereospecific epoxide-opening reactions of 1,1-dibromo-3,4-epoxy-1-alkenes with allyltributylstannane and with ketene silyl acetals in the presence of a Lewis acid are described. Both the reactions occurred regioselectively at the allylic position via an SN2 process giving rise to a single product, respectively. Treatment of the products by the latter reaction with p-TsOH afforded various 3,4-anti- and 3,4-syn-disubstituted γ-lactones in a highly stereoselective manner and high yields. |
| |
| Keywords: | Epoxide-opening reaction 1 1-Dibromo-3 4-epoxy-1-alkene Allyltributylstannane Ketene silyl acetal Lewis acid 3 4-Disubstituted γ-lactone |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
