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Synfacts 2008(2): 0169-0169  
DOI: 10.1055/s-2007-992444
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Cycloisomerization of 1,6-Enynes

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
F. Liu, Q. Liu, M. He, X. Zhang*, A. Lei
Wuhan University, P. R. of China and The Pennsylvania State University, University Park, USA
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Publikationsdatum:
23. Januar 2008 (online)

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Significance

The authors have previously reported the use of their second-generation [Rh(cod)Cl]2-BINAP-AgSbF6 system in cycloisomerization reactions to form lactones, lactams, and tetrahydrofurans (J. Am. Chem. Soc. 2002, 124, 8198). In the present work they report the application of this system to the cycloisomerization of 1,6-enynes to give functionalized cyclopentanes and cyclopenta­nones in high yields and excellent enantiomeric excesses. Furthermore, only 1,4-dienes were observed as products.