A general and stereospecific synthesis of trans-alkenes and regiospecific synthesis of ketones via stepwise hydroboration

…, D Basavaiah, SU Kulkarni

Index: Brown, Herbert C.; Basavaiah, D.; Kulkarni, Surendra U. Journal of Organic Chemistry, 1982 , vol. 47, # 19 p. 3808 - 3810

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Citation Number: 27

Abstract

Summary: The hydroboration of 1-bromo-1-alkynes with allrylbromoboranes (RBHBr. SMe2), conveniently obtained via the controlled hydridation of alkyldibromoboranes (RBBrz* SMe2), followed by treatment with sodium methoxide produces B-(trans-1-alkyl-1-alkeny1) boronate esters that provide the corresponding trans alkenes on protonolysis and ketones on oxidation.