Silver‐Catalyzed Epoxidation of Aldehydes Using Donor‐/ Acceptor‐type Vinyl Diazosuccinimides to Access Spiro‐Pyrrolidinedioneoxiranes

Abstract

A silver(I)‐catalyzed method to access spiro‐pyrrolidinedioneoxiranes has been developed. Silver hexafluoroantimonate was found to be an efficient catalyst for the epoxidation of aldehydes using donor‐/acceptor‐substituted vinyl diazosuccinimides as carbenoid precursors. The protocol has been found to be highly regio‐ and chemoselective, and works well with aromatic aldehydes containing electron‐withdrawing and ‐donating groups to afford spiro‐pyrrolidinedioneoxiranes with a broad substrate scope.