Division of Organic Chemistry , CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road , Pune 411008 , India.
Central NMR Facility , CSIR-National Chemical Laboratory , Pune 411008 , India.
Org Lett. 2018 May 4;20(9):2787-2791. doi: 10.1021/acs.orglett.8b00745. Epub 2018 Apr 26.
A Lewis acid catalyzed regioselective C-C bond is constructed through β-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama-Michael reaction of silyloxyfurans with p-QMs proceeds selectively through the α or γ position exclusively. The reaction is mild with broad substrate scope, thus allowing easy access to a wide range of bis-arylated α-/β-/γ-substituted butenolides.
路易斯酸催化的去共轭丁烯内酯与 p-醌甲基化物的β-加成反应,以 1,6-共轭加成的方式构建区域选择性 C-C 键。有趣的是,路易斯酸催化的硅氧基呋喃与 p-QM 的烯醇式 Mukaiyama-Michael 反应选择性地通过α或γ位进行。该反应条件温和,底物适用范围广,因此可以方便地获得广泛的双芳基-α-/β-/γ-取代的丁烯内酯。