期刊
TETRAHEDRON
卷 62, 期 18, 页码 4540-4548出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.02.043
关键词
zinc sulfinate; beta-hydroxy sulfone; epoxide; butadiene sulfone; butadienyl sulfones
Reaction of hydrophilic epoxides (ethylene oxide and propylene oxide) with readily accessible zinc sulfinates in aqueous solution under essentially neutral conditions afforded beta-hydroxy sulfones in good yields. This method avoids the need for organic solvents and produces ZnO as the only major reaction byproduct. 2-(Methylsulfonyl)ethanol, a common reagent for the protection of various functional groups, was obtained by this methodology from ethylene oxide in 78% yield. Reaction of various simple zinc alkane- and benzenesulfinates with propylene oxide proceeded regioselectively in 63-67% yield. The corresponding opening of these epoxides with zinc 1,3-butadiene-1-sulfinate afforded 1-butadienyl beta-hydroxyalkyl sulfones in 30% yield. Mechanistic studies revealed that the yields of these products were limited by their consumption in competing intra- and intermolecular Michael addition processes. (c) 2006 Elsevier Ltd. All rights reserved.
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