Gold-Catalyzed Nucleophilic Ring-Opening Reaction of 2-Alkynylazetidines with Alcohols

Abstract

The reaction of 2-alkynylazetidines and alcohols with a gold catalyst is described. A variety of substituted δ-amino-α,β-unsaturated ketones were synthesized via gold-promoted nucleophilic attack of alcohols followed by ring-opening of azetidine ring.

Advances in gold catalyzed synthesis of quinoid heteroaryls

“…This reaction produces damino-substituted a,b-unsaturated ketones. [69][70][71] When N-4nitrophenyl-substituted 2-alkynyl azetidines (2a) were heated, according to Touya Kariya et al, an unanticipated cascade reaction occurred, creating 2c by intramolecular Friedel-Crastype hydroarylation and Au-promoted ring-opening of the azetidine ring 72,73 in a single step (Scheme 5). The rst coordination of a gold complex to the alkynyl moiety resulted in the formation of the gold-alkyne complex A, which causes the cascade reaction of 2a to 2c.…”