alk-1-enyl sulfoxides is reported. The reaction between alane–pyridine complexes, triphenylphosphine, and sulfonyl chlorides affords the title products in good to excellent yields (70–94%) in short reaction times using mild conditions. The optimal ratio between reagents (alane–pyridine/PPh3/sulfonyl chloride 1.00/1.35/0.92) was obtained performing a chemiometric analysis. A rationale for the reaction was
Pyridine and triphenylphosphine oxide activation of sulfonyl chlorides in the syntheses of (E) alk-1-enyl sulfones
作者:G. Signore、C. Malanga、R. Menicagli
DOI:10.1016/j.tet.2008.09.056
日期:2008.12
This paper describes efficient and new approaches to (E) alk-1-enyl sulfones, starting from sulfonyl chloride/pyridine or sulfonyl chloride/triphenylphosphine complexes in the presence of (E) di-iso-butyl alk-1-enyl alanes.The use of CuCl in the presence of sulfonyl chloride/pyridine complexes or pyridine in the presence of sulfonyl chloride/triphenylphosphine complexes, respectively, results in a remarkable increase in the yields and conversions. (C) 2008 Elsevier Ltd. All rights reserved.