Phosphine triggered [3+2] allenoate-acrylate annulation: a mechanistic enlightenment

A mechanistic study of phosphine-mediated [3+2] annulation of allenoate and acrylate is presented. The insight gained has identified that (1) [3+2] cycloaddition proceeds through a stepwise mechanism and (2) the involvement of a molecule of water, which services as a proton-shuttle, is essential for annulated product formation. (C) 2007 Elsevier Ltd. All rights reserved.