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Synfacts 2006(8): 0809-0809  
DOI: 10.1055/s-2006-942016
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric [5+2] Cycloaddition of Vinylcyclopropanes and π-Systems

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
P. A. Wender*, L. O. Haustedt, J. Lim, J. A. Love, T. J. Williams, J.-Y. Yoon
Stanford University, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

Wender’s group has extended its [5+2] cycloaddition-reaction arsenal. They found that Rh(I)/BINAP is a superior catalyst for the cyclo­addition of vinylcyclopropanes tethered to alkenes for the intramolecular variant. The substrates containing synthetically useful sulfonamide and malono­diester groups gave high yields and excellent enantio­selectivities. Substitution at the cyclopropane group as well as internal substitution on the terminal alkene resulted in high selectivity. Alkyne-substituted substrates showed low ee values, as did a substrate with an internal hydrogen on the terminal alkene when the malonodiester was present in the tether.