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

Jia-Ming Hu^†, Jun-Qi Zhang^†, Bing-Bing Sun^†, Jun-Bo Chen^†, Jie-Qiang Yu^†,† Xiao-Peng Yang^†,† Hao-Peng Lv^†, Zheng Wang^*,‡（王正）, and Xing-Wang Wang^*,†（王兴旺）

^† Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

^‡ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Org. Lett.2019, 21, 8582--8586

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.

链接：https://pubs.acs.org/doi/10.1021/acs.orglett.9b03178