Journal of Organic Chemistry 2011-12-02

Base-controlled selective conversion of Michael adducts of malonates with enones in the presence of iodine.

Chun-Bao Miao, Min Zhang, Zong-Yong Tian, Hai-Tao Xi, Xiao-Qiang Sun, Hai-Tao Yang

Index: J. Org. Chem. 76(23) , 9809-16, (2011)

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Abstract

An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and α-hydroxylmalonate derivatives are obtained selectively using DBU, Na(2)CO(3), and NaOAc as the base, respectively. O(2) was identified to be crucial to the formation of oxetane and α-hydroxylmalonate derivatives.© 2011 American Chemical Society