Gold-catalyzed cycloisomerizations of ene-ynamides

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 di...

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Bibliographic Details
Published in:Tetrahedron 2009-02, Vol.65 (9), p.1809-1832
Main Authors: Couty, Sylvain, Meyer, Christophe, Cossy, Janine
Format: Article
Language:English
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Summary: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 α or β position of the nitrogen atom. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.108