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Issue 24, 2004
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Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

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Abstract

The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give enantiopure α-hydroxyacids, α-hydroxyesters or α-hydroxyamides by suitable choice of conditions.

Graphical abstract: Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

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Publication details

The article was received on 20 Aug 2004, accepted on 29 Sep 2004 and first published on 17 Nov 2004


Article type: Paper
DOI: 10.1039/B412788A
Citation: Org. Biomol. Chem., 2004,2, 3608-3617
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    Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

    S. V. Ley, E. Diez, D. J. Dixon, R. T. Guy, P. Michel, G. L. Nattrass and T. D. Sheppard, Org. Biomol. Chem., 2004, 2, 3608
    DOI: 10.1039/B412788A

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