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Alternative Sm(II) Species-Mediated Cascade Coupling/Cyclization for the Synthesis of Oxobicyclo[3.1.0]hexane-1-ols
Bingxin You1, Mengmeng Shen1, Guanqun Xie1,2
1Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University , Jinhua 321004, People's Republic of China.
Abstract:
The allylSmBr/HMPA/MsOH system has been found to be an efficient reagent for the "ester-alkene" coupling/cyclization cascade of readily available α-allyloxy esters. Oxobicyclo[3.1.0]hexane-1-ols were thus prepared in good to excellent yields and diastereoselectivities. Investigation on the mechanism suggested the possible existence of a new Sm(II) species, namely, CH3SO3SmBr, which resulted from the reaction between allylSmBr and MsOH and may be the actual SET reagent.
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