A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones
摘要：
In this article we describe a series of new asymmetric Michael reactions of carboxylate-3-substituted isoindolinones used as nucleophiles in the synthesis of valuable chiral tetrasubstituted derivatives. It has been shown that the reactivity and enantioselectivity strongly depend on the substitution pattern of the isoindolinone, requiring either cinchona-alkaloid based phase transfer catalysts or chiral hydrogen donors. Moreover, prolinol-TMS ether-based secondary amine catalysts permitted the development of Michael/cyclization tandem reaction with cynnamaldehyde for the synthesis of aza-polycyclic derivatives.
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关键词：
Nitrogen heterocycles Tetrasubstituted stereocenters Chiral phase transfer catalysis Bifunctional organocatalysis Iminium ion catalysis
DOI：
10.1016/j.tet.2016.12.036
被引量：
年份：
2017
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