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Issue 24, 2004
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Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides

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Abstract

Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation–reduction sequence. An usual double addition reaction of butane-2,3-diacetal protected glycolic acid to small aliphatic acid chlorides provides a synthetically useful, densely-functionalised lactone after acidic deprotection.

Graphical abstract: Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides

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Publication details

The article was received on 19 Aug 2004, accepted on 29 Sep 2004 and first published on 17 Nov 2004


Article type: Paper
DOI: 10.1039/B412790K
Citation: Org. Biomol. Chem., 2004,2, 3618-3627
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    Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides

    S. V. Ley, D. J. Dixon, R. T. Guy, M. A. Palomero, A. Polara, F. Rodríguez and T. D. Sheppard, Org. Biomol. Chem., 2004, 2, 3618
    DOI: 10.1039/B412790K

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