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Synfacts 2011(4): 0406-0406  
DOI: 10.1055/s-0030-1259670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Regio- and Diastereoselective [3+2] Cycloadditions

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
G. Yang*, Y. Shen, K. Li, Y. Sun, Y. Hua
Anhui Normal University, Wuhu, P. R. of China
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

The substituted tetrahydrofuran moiety can be found in a number of natural products possessing interesting biological properties. Quite a few reports describe 2,5-cis-diastereo­selective [3+2] cycloadditions of 2-substituted ­cyclopropane-1,1-diesters with aldehydes. In this work, trans-2,3-disubstituted cyclopropane-1,1-diesters are considered as substrates. While common 2,5-cis-products were obtained with electron-neutral and -poor aromatic aldehydes, electron-rich analogues furnished 2,5-trans-­adducts with excellent diastereoselectivities.