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Synfacts 2010(2): 0195-0195  
DOI: 10.1055/s-0029-1219093
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Gold(I)-Catalyzed Cycloisomerization of 1,6-Enynes to Bicyclo[4,1,0]heptenes

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet*
École Nationale Supérieure de Chimie de Paris, France
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

The authors have developed a gold(I)-catalyzed asymmetric cycloisomerization of 1,6-enynes. The desired bicyclo[4,1,0]heptenes of oxygen-tethered 1,6-enynes were obtained in excellent enantioselectivities, although the yields were low to moderate. They further extended this method to cycloisomerization of a nitrogen-tethered 1,6-enyne. It is interesting that the higher enantioselectivity was observed at higher tem­perature in the cycloisomerization of a nitrogen-tethered enyne.