This is the peer reviewed version of the following article: Chemistry – A European Journal 22.14 (2016): 4952 - 4959, which has been published in final form at http://doi.org/10.1002/chem.201504869. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived VersionsA silver-catalyzed 1,3-dipolar cycloaddition of fluorinated azomethine ylides and activated olefins is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of fluorinated pyrrolidines. Broad scope and high levels of diastereoselectivity have been achieved simply by using AgOAc/PPh3as the catalyst system. The high efficiency of the cycloaddition relies on the presence of a metal-coordinating group on the imine moiety, such as an ester or heteroaryl group. The asymmetric version of the cycloaddition has been developed by using Taniaphos as a chiral ligandFinancial support of this work by the Ministerio de Economía y
Competitividad (MINECO, CTQ2012-35790) is gratefully
acknowledge
