Stereoselective synthesis of enamides by a Peterson reaction manifold

A Fürstner; C Brehm; Y Cancho-Grande

doi:10.1021/ol016848p

Stereoselective synthesis of enamides by a Peterson reaction manifold

Org Lett. 2001 Nov 29;3(24):3955-7. doi: 10.1021/ol016848p.

Authors

A Fürstner¹, C Brehm, Y Cancho-Grande

Affiliation

¹ Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany. fuerstner@mpi-muelheim.mpg.de

PMID: 11720578
DOI: 10.1021/ol016848p

Abstract

Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN(3), and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimination process. This method is distinguished by its wide applicability and stereoselective course. [reaction: see text]