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Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine

Author:
Zhou, Jing, Bai, Lijuan, Liang, Guojuan, Chen, Yongjie, Gan, Zongjie, Wang, Wu, Zhou, Hui, Yu, Yu
Source:
RSC advances 2017 v.7 no.63 pp. 39885-39888
ISSN:
2046-2069
Subject:
X-radiation, catalytic activity, enantioselectivity, quinine
Abstract:
A new organocatalytic asymmetric domino Michael/O-alkylation reaction of maleimides with γ-halogenated-β-ketoesters catalyzed by simple, cheap, and commercially available quinine is described. The substrates are also commercially available. A variety of new chiral succinimide substituted 3(2H)-furanones were obtained in high yields (up to 94%) and good enantioselectivities (up to 94% ee). The absolute configuration of the new compound 4f was determined by single-crystal X-ray analysis and the proposed reaction pathway is also shown.
Agid:
6420914