异氰基乙酸酯与糖精衍生的1-氮杂二烯的有机催化不对称形式[3+2]环加成反应
Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of isocyanoacetates with saccharin-derived 1-azadienes.
作者信息
Chang Li, Zhu Guang-Yu, Yang Ting, Zhao Xiao-Li, Shi Min, Zhao Mei-Xin
机构信息
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, China.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
出版信息
Org Biomol Chem. 2021 Apr 28;19(16):3687-3697. doi: 10.1039/d1ob00115a.
An efficient organocatalytic diastereo- and enantioselective formal [3 + 2] cycloaddition reaction of α-isocyanoacetates with saccharin-derived 1-azadienes catalyzed by a dihydroquinine derived squaramide catalyst has been investigated, and it furnished the corresponding directly linked benzo[d]isothiazole 1,1-dioxide-dihydropyrroles with two adjacent tertiary-quaternary stereocenters in high yields (up to 98%), with moderate to excellent stereoselectivities (up to >20 : 1 dr and 97% ee) under mild conditions.
研究了由二氢奎宁衍生的方酰胺催化剂催化的α-异氰基乙酸酯与糖精衍生的1-氮杂二烯的高效有机催化非对映和对映选择性形式[3 + 2]环加成反应，该反应在温和条件下以高收率（高达98%）、中等至优异的立体选择性（高达>20:1的非对映选择性和97%的对映体过量）提供了具有两个相邻叔-季立体中心的相应直接相连的苯并[d]异噻唑1,1-二氧化物-二氢吡咯。
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