Issue 24, 2004

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Aug 2004
Accepted
29 Sep 2004
First published
17 Nov 2004

Org. Biomol. Chem., 2004,2, 3618-3627

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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