Pd(II)/N,N’-Disulfonyl Bisimidazoline-Catalyzed Enantioselective Synthesis of Cyclic Quaternary Centers and Mechanistic Investigations

Yu-Xin Wang,¹ Chen-Long Li,¹ Yin-Ping Liu, Wen-Juan Hao, Zhi-Xiang Yu,* Bo Jiang*

A Pd(II)/N,N′-disulfonyl bisimidazoline-catalyzedasymmetric 1,4-conjugate addition reaction of low-cost arylboronic acids with readily availableβ-substituted cyclic enones is described, providing a straightforward way of constructing cyclic all-carbon quaternary stereocenters with high enantioselectivity, in which ≥96% ee was obtained in most cases. The reaction proceeded without the protection of inert gas, making the operation process simple. Theoretical calculations have been applied to understandthe origins of enantioselectivity.

J. Org. Chem. 2024, 89, 9381-9388; DOI: 10.1021/acs.joc.4c00636