Asymmetric Formal Coupling of β-Ketoesters with Quinones Promoted by a Chiral Bifunctional N-Heterocyclic Olefin

• DOI: 10.1021/acs.orglett.3c02885
• Publication Date: 2023-09-26T13:05:42Z
• Authors: Sijing Wang; Jia Yang; Hongkun Zeng; Yuqiao Zhou; Fei Wang; Xiaoming Feng; Shunxi Dong
• Keywords: Formal synthesis

A highly enantioselective formal coupling of β-ketoesters with quinones was accomplished by a chiral bifunctional N-heterocyclic olefin organocatalyst. With as low 1 mol % catalyst loading, number enantioenriched quinone derivatives were afforded in good yields high enantioselectivities and regioselectivities (up to 96% yield, 98% ee, 19:1 rr). Gram-scale synthesis the inhibitory effect several products on viability cancer cells demonstrate potential utility current method.