Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars |
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Authors: | M.V. Berrocal,E. Romá n,J.A. Serrano,M.E. Light |
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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 |
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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. |
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Keywords: | Michael addition Aldol cyclization Nitro compounds Sugars |
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