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Synfacts 2006(1): 0048-0048
DOI: 10.1055/s-2005-921680
DOI: 10.1055/s-2005-921680
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes and Alkynes
T. Shibata*, Y. Arai, Y-K. Tahara
Waseda University, Tokyo, Japan
Further Information
Publication History
Publication Date:
16 December 2005 (online)
![](https://www.thieme-connect.de/media/synfacts/200601/lookinside/thumbnails/10.1055-s-2005-921680-1.jpg)
Significance
Enantioselective [2+2+2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing a chiral quaternary center. In all cases, the enantioselectivity was high and yields were moderate to good. A range of alkynes was tolerated, including acetylene and also an unprotected diol. Use of unsymmetrical alkynes resulted in a mixture of regioisomers (4:1 to 7:1). O, N and C-bridged enynes were also applied to the reaction.