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

Steven V. Ley; Darren J. Dixon; Richard T. Guy; Maria A. Palomero; Alessandra Polare; Félix Rodríguez; Tom D. Sheppard

doi:10.1039/b412790k

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

Steven V. Ley, Darren J. Dixon, Richard T. Guy, Maria A. Palomero, Alessandra Polare, Félix Rodríguez, Tom D. Sheppard

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

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.

Original language	English
Pages (from-to)	3618-3627
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	24
DOIs	https://doi.org/10.1039/b412790k
Publication status	Published - 21 Dec 2004

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Ley, S. V., Dixon, D. J., Guy, R. T., Palomero, M. A., Polare, A., Rodríguez, F., & Sheppard, T. D. (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. Organic and Biomolecular Chemistry, 2(24), 3618-3627. https://doi.org/10.1039/b412790k

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title = "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.",

author = "Ley, {Steven V.} and Dixon, {Darren J.} and Guy, {Richard T.} and Palomero, {Maria A.} and Alessandra Polare and F{\'e}lix Rodr{\'i}guez and Sheppard, {Tom D.}",

year = "2004",

month = dec,

day = "21",

doi = "10.1039/b412790k",

language = "English",

volume = "2",

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journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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Ley, SV, Dixon, DJ, Guy, RT, Palomero, MA, Polare, A, Rodríguez, F & Sheppard, TD 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', Organic and Biomolecular Chemistry, vol. 2, no. 24, pp. 3618-3627. https://doi.org/10.1039/b412790k

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. / Ley, Steven V.; Dixon, Darren J.; Guy, Richard T. et al.
In: Organic and Biomolecular Chemistry, Vol. 2, No. 24, 21.12.2004, p. 3618-3627.

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

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T1 - 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

AU - Ley, Steven V.

AU - Dixon, Darren J.

AU - Guy, Richard T.

AU - Palomero, Maria A.

AU - Polare, Alessandra

AU - Rodríguez, Félix

AU - Sheppard, Tom D.

PY - 2004/12/21

Y1 - 2004/12/21

N2 - 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.

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UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/cc8fd46&sid=DataCite

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DO - 10.1039/b412790k

M3 - Article

SN - 1477-0520

VL - 2

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EP - 3627

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

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

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