Catalytic asymmetric Michael and Nef-type sequential reaction of nitroolefin with azlactone to construct oxazole-fused succinimide.

Chem Commun (Camb)

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.

Published: November 2024

A series of oxazole-fused succinimides bearing vicinal quaternary carbon centers were synthesized. This process takes place between nitroolefins and azlactones in the presence of a bifunctional chiral guanidine-sulfonamide organocatalyst, followed by a Nef-type transformation under the treatment of DMAP/AcO. Several control experiments were conducted to propose the mechanism.

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http://dx.doi.org/10.1039/d4cc04858jDOI Listing

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