Enantiopure thiosulfonium salts in asymmetric synthesis. Face selectivity in electrophilic additions to unfunctionalised olefins
作者:Vittorio Lucchini、Giorgio Modena、Lucia Pasquato
DOI:10.1039/c39940001565
日期:——
Enantiopure S-methylthiodinaphtho[2,1-c: 1′,2′-e][1,2]dithiinium hexachloroantimonate 3, transfers enantioselectively the MeS+ group to trans-hex-3-ene, leading to non-racemic thiiranium ion 4, which, in turn, reacts with MeCN–H2O allowing the synthesis of optically active double functionalised alkanes with enantiomeric excesses of up to 86%.
对映纯的S-甲基硫代萘[2,1-c: 1′,2′-e][1,2]二硫铵六氯锑盐3,以对映选择性的方式将MeS+基团转移到反式-己-3-烯,生成非外消旋的硫烯离子4,后者与MeCN–H2O反应,允许合成具有高达86%对映体过剩的光学活性双功能烃。