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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
Rh-Catalyzed Highly Enantioselective Formation of Functionalized Cyclopentanes and Cyclopentanones
Org. Biomol. Chem.  2007,  5:  3531-3534  
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Publication History

Publication Date:
23 January 2008 (online)

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Key words

rhodium - Alder-ene reaction - cyclopentanes - cyclopentanones

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.

Comment

Cyclopentanes and cyclopentanones serve as basic skeletons for numerous natural and synthetic organic molecules. Furthermore, the utility of Rh-catalyzed cycloisomerization reactions was recently showcased in Nicolaou’s total synthesis of platensimycin (Angew. Chem. Int. Ed. 2006, 45, 7086). The authors demonstrated the utility of the present method with a highly selective synthesis of (+)-(1S,2S)-dihydrojasmonate.

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