Tetrahedron Letters

Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane

HI Kong, JE Crichton, JM Manthorpe

Index: Kong, Han Il; Crichton, Jennifer E.; Manthorpe, Jeffrey M. Tetrahedron Letters, 2011 , vol. 52, # 29 p. 3714 - 3717

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Citation Number: 11

Abstract

Abstract α-Trifluoromethanesulfonyl esters, ketones and amides are C–H acids capable of reacting with trimethylsilyldiazomethane to afford the corresponding ambiphilic alkenes. While esters were found to be non-selective, ketones were highly regioselective for O- methylation and displayed variable E/Z stereoselectivity. Amides were observed to be both highly regio-and stereoselective, affording O-methylation with exclusive formation of the Z- ...