Thermodynamics versus kinetics in hetero-Michael cyclizations: a highly stereoselective approach to access both epimers of a C-D-mannopyranoside

Abstract : A simple method for the stereocontrolled synthesis of both alpha and beta pseudo-anomers of a thio-functionalized C-glycoside is described. A 2,3:4,6-di-O-isopropylidene manno scaffold is employed to allow a strict control of the diastereoselectivity of the base-catalyzed intramolecular hetero-Michael addition of an alcohol to a vinyl sulfone, by simply changing the temperature of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.
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Vincent Aucagne, A. Tatibouët, Patrick Rollin. Thermodynamics versus kinetics in hetero-Michael cyclizations: a highly stereoselective approach to access both epimers of a C-D-mannopyranoside. Tetrahedron Letters, Elsevier, 2008, 49, pp.4750-4753. ⟨10.1016/j.tetlet.2008.05.117⟩. ⟨hal-00512453⟩

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