Tandem Michael addition and intramolecular aldol cyclization of 1,2-dideoxy-1-nitroheptitols derived from sugars

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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