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Synfacts 2009(5): 0532-0532  
DOI: 10.1055/s-0029-1216626
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Constructing Polycyclic Compounds via Formal [4+1] Cycloaddition

Contributor(s): Hisashi Yamamoto, Zhi Li
R. W. Coscia, T. H. Lambert*
Columbia University, New-York, USA
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

The authors developed an indirect [4+1] approach in synthesizing polycyclic cyclopentene derivatives. The transformation consists of Pd(OAc)2-catalyzed diastereoselective oxidative cyclopropanation of 1,3-dienyl β-keto esters and MgI2-promoted rearrangement of the intermediates into the desired cyclopentenes.