He Fu-Sheng, Zhang Chun, Jiang Minghui, Lou Lujun, Wu Jie, Ye Shengqing
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University 1139 Shifu Avenue Taizhou 318000 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China.
Chem Sci. 2022 Jul 8;13(30):8834-8839. doi: 10.1039/d2sc02497g. eCollection 2022 Aug 4.
An organocatalytic enantioselective radical reaction of potassium alkyltrifluoroborates, DABCO·(SO) and α,β-unsaturated carbonyl compounds under photoinduced conditions is developed, which provides an efficient pathway for the synthesis of chiral β-sulfonyl carbonyl compounds in good yields with excellent enantioselectivity (up to 96% ee). Aside from α,β-unsaturated carbonyl compounds with auxiliary groups, common chalcone substrates are also well compatible with this organocatalytic system. This method proceeds through an organocatalytic enantioselective radical sulfonylation under photoinduced conditions, and represents a rare example of asymmetric transformation involving sulfur dioxide insertion.
开发了一种在光诱导条件下烷基三氟硼酸钾、DABCO·(SO)与α,β-不饱和羰基化合物的有机催化对映选择性自由基反应，该反应为合成手性β-磺酰基羰基化合物提供了一条有效途径，产率良好，对映选择性优异（高达96% ee）。除了带有辅助基团的α,β-不饱和羰基化合物外，常见的查尔酮底物也能很好地与该有机催化体系兼容。该方法通过光诱导条件下的有机催化对映选择性自由基磺酰化反应进行，是涉及二氧化硫插入的不对称转化的罕见例子。
