Chiral N-Heterocyclic-Carbene-Catalyzed Cascade Asymmetric Desymmetrization of Cyclopentenediones with Enals: Access to Optically Active 1,3-Indandione Derivatives

• DOI: 10.1021/acs.orglett.9b03178
• Publication Date: 2019-10-16T21:45:24Z
• Authors: Jia-Ming Hu; Jun-Qi Zhang; Bing-Bing Sun; Jun-Bo Chen; Jie-Qiang Yu; Xiao-Peng Yang; Hao-Peng Lv; Zheng Wang; Xing-Wang Wang
• Keywords: 01 natural sciences; 0104 chemical sciences

A chiral N-heterocyclic-carbene-catalyzed cascade asymmetric desymmetrization reaction of cyclopentenediones with enals has been successfully initiated, followed with tandem aldol annulation, aromatization, as well as sequential methylation. The reactions proceeded well under mild reaction conditions, with broad substrate scope and good functional group tolerance, providing a rapid access to highly functionalized chiral 2,2-disubstituted 1,3-indandione derivatives containing an all-carbon quaternary stereogenic center in moderate to good yields with high enantioselectivities.