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Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars
Authors:M.V. Berrocal,E. Romá  n,J.A. Serrano,M.E. Light
Affiliation:a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, 06071 Badajoz, Spain
b Department of Chemistry, University of Southampton, Southampton SO17 1BJ, UK
Abstract:The base-catalyzed Michael addition of primary nitro compounds derived from sugars with 2 equiv of methyl vinyl ketone or acrolein was followed, in situ, by an asymmetric intramolecular aldol cyclization, thus yielding 2-acyl-4-glyco-4-nitrocyclohexanol derivatives with high diastereoselectivity.
Keywords:Michael addition   Aldol cyclization   Nitro compounds   Sugars
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