2009 · TETRAHEDRON

Gold-catalyzed cycloisomerizations of ene-ynamides

Couty, Sylvain, Meyer, Christophe, Cossy, Janine

Journal
TETRAHEDRON
Année
2009
Volume
65
Numéro
9
Pages
1809-1832
Mois
FEB 28
DOI
10.1016/j.tet.2008.10.108

Abstract

The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl Substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine Subunit from Substrates possessing a propargylic alcohol moiety. High diastereoselectivities are observed with 1,6-ene-ynamides having a stereocenter at the or alpha or beta position of the nitrogen atom. (C) 2008 Elsevier Ltd. All rights reserved.

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