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Organocatalytic Enantioselective Michael–Michael–Michael–Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles
Organic Letters ( IF 4.9 ) Pub Date : 2017-11-01 00:00:00 , DOI: 10.1021/acs.orglett.7b02962
Prakash D. Chaudhari,Bor-Cherng Hong,Gene-Hsiang Lee

An organocatalyzed enantioselective Michael–Michael–Michael–aldol cascade reaction for the construction of cyclopentane fused spirooxindoles was achieved. The domino reaction provided the spirooxindoles with six contiguous stereocenters including a quaternary center in good yields (55–64%) with excellent enantioselectivities (up to >99% ee). Enantioselective Michael–Michael–Michael–aldol condensation–aromatization reactions of an isomeric product were observed.

中文翻译:

有机催化对映选择性Michael–Michael–Michael–Aldol缩合反应:四级联多不对称合成多取代螺环氧化吲哚中的六个立体中心的控制。

实现了有机催化的对映体选择性迈克尔-迈克尔-迈克尔-奥尔多级联反应,用于构建环戊烷稠合的螺氧并吲哚。多米诺骨牌反应为螺硫醇提供了六个连续的立体中心,包括一个具有良好对映选择性(高达> 99%ee)的高产(55-64%)的四元中心。观察到异构产物的对映选择性迈克尔-迈克尔-迈克尔-醛醇缩合-芳香化反应。
更新日期:2017-11-01
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