Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine†
Jing Zhou,Lijuan Bai,Guojuan Liang,Yongjie Chen,Zongjie Gan,Wu Wang,Hui Zhou,Yu Yu
RSC Advances Pub Date : 08/16/2017 00:00:00 , DOI:10.1039/C7RA07317H
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.

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