Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine. Issue 63 (16th August 2017)

• Record Type: Journal Article
• Authors: Zhou, Jing; Bai, Lijuan; Liang, Guojuan; Chen, Yongjie; Gan, Zongjie; Wang, Wu; Zhou, Hui; Yu, Yu
• Is Part Of: RSC advances. Volume 7:Issue 63(2017)
• Page Start: 39885
• Page End: 39888
• Publication Date: 2017-08-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra07317h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Asymmetric domino reaction of maleimides with γ-halogenated-β-ketoesters catalyzed by quinine is developed to give succinimide substituted 3(2 H )-furanones in good enantioselectivities. 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(2 H )-furanones were obtained in high yields (up to 94%) and good enantioselectivities (up to 94% ee). The absolute configuration of the new compound4f was determined by single-crystal X-ray analysis and the proposed reaction pathway is also shown.