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Highly Regio- and Diastereoselective [3+2] Cycloadditions
G. Yang*, Y. Shen, K. Li, Y. Sun, Y. Hua
Anhui Normal University, Wuhu, P. R. of China
18 March 2011 (online)
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.