A systematic study on the use of different organocatalytic activation modes for asymmetric conjugated addition reactions of isoindolinones

详细信息    查看全文

• 作者：Francesco Scorzelli^a ; Antonia Di Mola^b ; Francesco De Piano^a ; Consiglia Tedesco^a ; Laura Palombi^a ; Rosanna Filosa^c ; Mario Waser^d ; Antonio Massa^a ; ^{amassa@unisa.it}
• 关键词：Nitrogen heterocycles ; Tetrasubstituted stereocenters ; Chiral phase transfer catalysis ; Bifunctional organocatalysis ; Iminium ion catalysis
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：16 February 2017
• 年：2017
• 卷：73
• 期：7
• 页码：819-828
• 全文大小：785 K
• 卷排序：73

文摘

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 bifunctional tertiary amines organocatalysts. 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.