Department of Chemistry, South University of Science and Technology of China , 1088 Xueyuan Boulevard, Nanshan District, Shenzhen, Guangdong 518055, China.
Org Lett. 2017 Sep 15;19(18):4774-4777. doi: 10.1021/acs.orglett.7b02144. Epub 2017 Aug 28.
A reaction has been developed for the chiral phosphine-catalyzed enantioselective [1 + 4] annulation of Morita-Baylis-Hillman carbonates with electron-deficient olefins via a Michael alkylation process. Morita-Baylis-Hillman carbonates reacted smoothly with β,γ-unsaturated α-keto ester and α,β-unsaturated ketone substrates under 1,2-bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide catalysis to furnish a wide range of optically active 2,3-dihydrofurans in high yields (up to 95%) with excellent asymmetric induction (up to >99% ee, >20:1 dr). This protocol represents an efficient strategy for the synthesis of optically active multifunctional 2,3-dihydrofurans via an asymmetric Michael alkylation domino reaction.
已经开发出一种手性膦催化的 Morita-Baylis-Hillman 碳酸酯与缺电子烯烃的对映选择性 [1 + 4] 环加成反应，通过迈克尔烷基化过程。在 1,2-双[(2R,5R)-2,5-二甲基磷杂环戊烷]苯并氧化物催化下，Morita-Baylis-Hillman 碳酸酯与β,γ-不饱和α-酮酯和α,β-不饱和酮底物顺利反应，以高收率（高达 95%）和优异的对映体诱导（高达 >99%ee，>20:1dr）得到广泛的光学活性 2,3-二氢呋喃。该方案代表了通过不对称迈克尔烷基化级联反应合成光学活性多功能 2,3-二氢呋喃的有效策略。
