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

doi:10.1021/jo061254r

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

J Org Chem. 2006 Dec 8;71(25):9366-72. doi: 10.1021/jo061254r.

Authors

Sang Ick Lee¹, Soo Min Kim, Mi Ra Choi, Sun Young Kim, Young Keun Chung, Won-Sik Han, Sang Ook Kang

Affiliation

¹ Intelligent Textile System Research Center, Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.

PMID: 17137363
DOI: 10.1021/jo061254r

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.