Tetrahedron

Acid catalyzed rearrangement of vinyl and ketene acetals

E Maziarz, B Furman

Index: Maziarz, Elzbieta; Furman, Bartlomiej Tetrahedron, 2014 , vol. 70, # 8 p. 1651 - 1658

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Abstract

Abstract Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.

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