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

SV Ley, E Diez, DJ Dixon, RT Guy, P Michel…

Index: Ley, Steven V.; Diez, Elena; Dixon, Darren J.; Guy, Richard T.; Michel, Patrick; Nattrass, Gillian L.; Sheppard, Tom D. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 24 p. 3608 - 3617

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Citation Number: 41

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.

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