Au(I)-Catalyzed Cyclization of Enynes Bearing an Olefinic Cycle

Gold(I)-catalyzed cyclization of enynes containing an olefinic cycle has been studied. The introduction of an olefinic ring instead of a terminal alkene in enynes dramatically increased the yield of the reaction. Enynes having an olefinic cycle were prepared by a rhodium-catalyzed intermolecular [4...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-12, Vol.71 (25), p.9366-9372
Main Authors: Lee, Sang Ick, Kim, Soo Min, Choi, Mi Ra, Kim, Sun Young, Chung, Young Keun, Han, Won-Sik, Kang, Sang Ook
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary:Gold(I)-catalyzed cyclization of enynes containing an olefinic cycle has been studied. The introduction of an olefinic ring instead of a terminal alkene in enynes dramatically increased the yield of the reaction. Enynes having an olefinic cycle were prepared by a rhodium-catalyzed intermolecular [4 + 2] cycloaddition of diynes with butadiene. Consecutive rhodium-catalyzed Diels−Alder/gold(I)-catalyzed cycloisomerization reactions were integrated in a one-pot reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061254r