Oxa-π, σ-Methane Rearrangement Approach for Epoxide Synthesis

Abstract

Epoxides are significant chemicals that are utilized across various fields. Here, we describe an unprecedented photochemical rearrangement approach for synthesizing a diverse collection of epoxides enabled by energy transfer catalysis under visible light conditions. The process enables the easy preparation of α-amino-substituted epoxide derivatives with a broad substrate scope, functional group tolerance, and mild reaction conditions. Furthermore, this photorearrangement has also been applied in complex architectures, and the epoxides could be easily transferred to amino alcohol derivatives. Overall, this oxa-π, σ-methane rearrangement provides a complementary strategy to the existing methods of photochemical rearrangement through energy transfer catalysis.