Highly Effective Vinylogous Mukaiyama−Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane

Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) performed as an excellent acid catalyst for the vinylogous Mukaiyama−Michael reaction of α,β-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted γ-butenolide structure.

由1,1,3,3-四(三氟甲磺酰基)丙烷（1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane，简称Tf2CHCH2CHTf2）原位生成的甲硅基物种（silyl methide species），可作为性能优异的酸催化剂，用于α,β-不饱和酮与2-硅氧基呋喃的插烯Mukaiyama-迈克尔反应（vinylogous Mukaiyama−Michael reaction）。值得注意的是，为以合理收率获得1,4-加成产物，所需的Tf2CHCH2CHTf2负载量极低，范围为0.05至1.0 mol%。该碳酸介导的插烯Mukaiyama-迈克尔反应，为构建高度取代的γ-丁内酯结构提供了一种强有力的合成方法学。