Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes and ynamides

Ruthenium-catalyzed [2+2] cycloadditions between bicyclic alkenes and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%). Diastereosel...

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Bibliographic Details
Published in:Tetrahedron 2006-04, Vol.62 (16), p.3823-3836
Main Authors: Villeneuve, Karine, Riddell, Nicole, Tam, William
Format: Article
Language:English
Subjects:
Amidation
Cycloaddition
Ynamines
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Summary:Ruthenium-catalyzed [2+2] cycloadditions between bicyclic alkenes and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%). Diastereoselective cycloaddition utilizing chiral cyclic ynamides were also examined and a low to moderate level of asymmetric induction was observed. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.081