通过催化顺序 1,6-加成/α-异氰基乙酸酯与对醌甲醚的酯交换反应不对称合成二氢香豆素。
Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides.
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.
Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
出版信息
Org Biomol Chem. 2020 Feb 26;18(8):1637-1646. doi: 10.1039/c9ob02652e.
A catalytic asymmetric synthesis of 3,4-dihydrocoumarins with adjacent tertiary-quaternary stereocenters by 1,6-addition/transesterification cascade reaction of α-isocyanoacetates with ortho-hydroxyphenyl-substituted para-quinone methides (p-QMs) has been developed. Using a combination of dihydroquinidine-derived aminophosphine and silver nitrate as a binary catalytic system, moderate to good yields, excellent diastereoselectivities (>20 : 1 dr) and good to excellent enantioselectivities (up to 94% ee) were achieved for a wide range of isocyanoacetates and p-QMs.
通过α-异氰基乙酸酯与邻羟基苯取代的对醌甲川（p-QM）的 1,6-加成/酯交换级联反应，开发了具有相邻叔-季立体中心的 3,4-二氢香豆素的催化不对称合成。使用二氢奎宁衍生的氨基膦和硝酸银的组合作为二元催化体系，对于广泛的异氰基乙酸酯和 p-QM，实现了中等至良好的产率、优异的非对映选择性（>20:1 dr）和良好至优异的对映选择性（高达 94%ee）。
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