Journal of Organic Chemistry 2006-12-08

Au(I)-catalyzed cyclization of enynes bearing an olefinic cycle.

Sang Ick Lee, Soo Min Kim, Mi Ra Choi, Sun Young Kim, Young Keun Chung, Won-Sik Han, Sang Ook Kang

Index: J. Org. Chem. 71 , 9366, (2006)

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Abstract

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.