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

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 alpha-hydroxyacids, alpha-hydroxy...

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Veröffentlicht in:	Organic & biomolecular chemistry 2004-12, Vol.2 (24), p.3608-3617
Hauptverfasser:	Ley, Steven V, Diez, Elena, Dixon, Darren J, Guy, Richard T, Michel, Patrick, Nattrass, Gillian L, Sheppard, Tom D
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetals - chemical synthesis Acetals - chemistry Alkylation Amides - chemical synthesis Amides - chemistry Hydroxy Acids - chemical synthesis Hydroxy Acids - chemistry Molecular Conformation Stereoisomerism
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Beschreibung
Zusammenfassung:	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 alpha-hydroxyacids, alpha-hydroxyesters or alpha-hydroxyamides by suitable choice of conditions.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/b412788a