期刊
TETRAHEDRON
卷 60, 期 38, 页码 8357-8361出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.07.022
关键词
Baylis-Hillman adducts; (Z)- and (E)-allyl bromides and iodides; metallic halides; NaHSO4 center dot SiO2; stereochemistry
A simple, mild and efficient stereoselective synthesis of (Z)- and (E)-allyl bromides and iodides has been developed by treatment of the Baylis-Hillman adducts with lithium bromide and iodide, respectively, in methylene chloride catalyzed by silica supported sodium hydrogen sulfate at room temperature. The role of various solvents, different reacting metallic halides, nature of the adducts and activity of several heterogeneous catalysts on the yields and stereochemistry of the products have been thoroughly studied. (C) 2004 Elsevier Ltd. All rights reserved.
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