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Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs. nitrone route

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Abstract

A dual synthetic strategy to afford 2-substituted trihydroxypiperidines is disclosed. The procedure involved Grignard addition either to a carbohydrate-derived aldehyde or to a nitrone derived thereof, and took advantage of an efficient ring-closure reductive amination strategy in the final cyclization step. An opposite diastereofacial preference was demonstrated in the nucleophilic attack to the two electrophiles, which would finally produce the same piperidine diastereoisomer as the major product. However, use of a suitable Lewis acid in the Grignard addition to the nitrone allowed reversing the selectivity, giving access to 2-substituted piperidines with the opposite configuration at C-2.

Graphical abstract: Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs. nitrone route

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Publication details

The article was received on 26 Jul 2017, accepted on 10 Oct 2017 and first published on 11 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB01848G
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs. nitrone route

    S. Mirabella, G. Fibbi, C. Matassini, C. Faggi, A. Goti and F. Cardona, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01848G

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