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(3S,4R)-3,4-Dihydroxy-N-alkyl-L-homoprolines: Synthesis and Computational Mechanistic Studies

Abstract

This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-L-homoprolines described so far. 2,4-O-Benzylidene-D-erythrose was obtained from D-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-L-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-lactone intermediates was studied by computational means either in acidic and basic conditions. The theoretical mechanism’s studies full explain the experimental results: a) an equilibrium between L-homoprolines and its bicyclic counterpart is established in acid; b) the equilibrium suffers a complete displacement towards the L-homoprolines side in basic medium.

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Publication details

The article was received on 03 Oct 2019, accepted on 05 Nov 2019 and first published on 08 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02141H
Org. Biomol. Chem., 2019, Accepted Manuscript

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    (3S,4R)-3,4-Dihydroxy-N-alkyl-L-homoprolines: Synthesis and Computational Mechanistic Studies

    D. S. Freitas, C. E. A. Sousa, J. C. Parente, A. Drogalin, A. Gil Fortes, N. M. F. S. A. Cerqueira and M. J. Alves, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02141H

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