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

Steven V. Ley; Elena Diez; Darren J. Dixon; Richard T. Guy; Patrick Michel; Gillian L. Nattrass; Tom D. Sheppard

doi:10.1039/b412788a

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

Steven V. Ley
, Elena Diez
, Darren J. Dixon
, Richard T. Guy
, Patrick Michel
, Gillian L. Nattrass
, Tom D. Sheppard

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3608-3617
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	24
DOIs	https://doi.org/10.1039/b412788a
Publication status	Published - 21 Dec 2004

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10.1039/b412788a

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

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.",

author = "Ley, \{Steven V.\} and Elena Diez and Dixon, \{Darren J.\} and Guy, \{Richard T.\} and Patrick Michel and Nattrass, \{Gillian L.\} and Sheppard, \{Tom D.\}",

year = "2004",

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doi = "10.1039/b412788a",

language = "English",

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T1 - Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

AU - Ley, Steven V.

AU - Diez, Elena

AU - Dixon, Darren J.

AU - Guy, Richard T.

AU - Michel, Patrick

AU - Nattrass, Gillian L.

AU - Sheppard, Tom D.

PY - 2004/12/21

Y1 - 2004/12/21

N2 - 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.

AB - 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.

U2 - 10.1039/b412788a

DO - 10.1039/b412788a

M3 - Article

SN - 1477-0520

VL - 2

SP - 3608

EP - 3617

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

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

Abstract

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