Pyridine-Catalyzed Addition of Diary 1-1,2-diones to Dimethyl Butynedioate Leading to the Formation of 1,2-Diaroyl Dimethyl Maleates via an Unprecedented Rearrangement

摘要

Pyridine catalyzes the reaction of 1,2-diaryl diones with dimethyl butynedioate to afford diaroyl maleates.This unprecedented rearrangement involves a unique benzoyl migration and proceeds with complete stereoselectivity.In the course of our recent explorations of the reactivity of zwitterions derived from nucleophilic species and activated acetylenes,we happened upon a fascinating reaction that is tantamount to the trans addition of aldehydes to the triple bond of dimethyl butynedioate leading to 1-aroyl fumarates(Scheme I).