Tetrahedron letters

Intramolecular metal-catalyzed amination of pseudo-anomeric C–H bonds

S Toumieux, P Compain, OR Martin

Index: Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R. Tetrahedron Letters, 2005 , vol. 46, # 28 p. 4731 - 4735

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Citation Number: 25

Abstract

Intramolecular metal-catalyzed amination of a pseudo-anomeric C–H bond in a C-glycoside is reported. Treatment of α, β-C-carbamoyloxymethyl-or β-C-sulfamoyloxymethyl glycosides with Rh2 (OAc) 4, PhI (OAc) 2, and MgO provided original spirooxazolidines or spirooxathiazolidines in reasonable yields. No correlation between 'anomeric' stereochemistry and insertion efficiency was found for the conversion of carbamate ...