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-hydroxyesters or alpha-hydroxyamides by suitable choice of conditions.
Ley
Steven V
SV
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW. svl1000@cam.ac.uk
Diez
Elena
E
Dixon
Darren J
DJ
Guy
Richard T
RT
Michel
Patrick
P
Nattrass
Gillian L
GL
Sheppard
Tom D
TD
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000080:Acetals; D000577:Amides; D006880:Hydroxy Acids; C442342:butane-2,3-diacetal glycolic acid