4-Endo-Trig Cyclization Processes Using Bis(collidine)bromine(I) Hexafluorophosphate as Reagent: Preparation of 2-Oxetanones, 2-Azetidinones, and Oxetanes.

Abstract

Reaction in methylene chloride of bis(collidine)bromine(I) hexafluorophosphate with alpha,beta-unsaturated acids and alpha,beta-unsaturated N-sulfonamides was found to lead diastereospecifically to the corresponding 2-oxetanones and 2-azetidinones in moderate yields (23-60%), by an almost unknown 4-endo cyclization. This process allow the synthesis of these interesting classes of products in one step from common substrates. Similarly, the reaction of cinnamic alcohols led, by the same cyclization procedure, to oxetanes (20-36%); the presence of a gem-dimethyl group in alpha of the alcohol function appeared beneficial.