Silver-Catalyzed 7-exo-dig Cyclization of Silylenolether-ynesulfonamides

Clément F Heinrich; Indira Fabre; Laurence Miesch

doi:10.1002/anie.201510708

Silver-Catalyzed 7-exo-dig Cyclization of Silylenolether-ynesulfonamides

Angew Chem Int Ed Engl. 2016 Apr 18;55(17):5170-4. doi: 10.1002/anie.201510708. Epub 2016 Mar 22.

Authors

Clément F Heinrich¹, Indira Fabre², Laurence Miesch³

Affiliations

¹ Laboratoire de Chimie Organique Synthétique, Institut de Chimie, 1, rue Blaise Pascal, BP296/R8, 67008, Strasbourg, France.
² Département de Chimie, Ecole Normale Supérieure-PSL Research University, Sorbonne Universités-UPMC Univ Paris 06, CNRS UMR 8640 PASTEUR, 24, rue Lhomond, 75005, Paris, France.
³ Laboratoire de Chimie Organique Synthétique, Institut de Chimie, 1, rue Blaise Pascal, BP296/R8, 67008, Strasbourg, France. [email protected].

PMID: 27000724
DOI: 10.1002/anie.201510708

Abstract

Cyclization of silylenolether-ynesulfonamides proceeds at ambient temperature under mild reaction conditions under silver catalysis. Bridged compounds were obtained exclusively through 7-exo-dig reactions. The protocol is applicable to a wide range of substrates, thus leading to azabicyclic frameworks.

Keywords: cyclizations; heterocycles; silver; structure elucidation; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't