Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction

David J Phillips; Kathryn S Pillinger; Wei Li; Angela E Taylor; Andrew E Graham

doi:10.1039/b602329k

Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction

David J Phillips, Kathryn S Pillinger, Wei Li, Angela E Taylor, Andrew E Graham

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

27 Citations (Scopus)

Abstract

Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.

Original language	English
Pages (from-to)	2280-2
Number of pages	3
Journal	Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/b602329k
Publication status	Published - 4 Jun 2006

Keywords

Alkenes
Butylene Glycols
Chemistry, Organic
Esters
Manganese Compounds
Organic Chemistry Phenomena
Oxidation-Reduction
Oxides
Stereoisomerism

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10.1039/b602329k

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title = "Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction",

abstract = "Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.",

keywords = "Alkenes, Butylene Glycols, Chemistry, Organic, Esters, Manganese Compounds, Organic Chemistry Phenomena, Oxidation-Reduction, Oxides, Stereoisomerism",

author = "Phillips, {David J} and Pillinger, {Kathryn S} and Wei Li and Taylor, {Angela E} and Graham, {Andrew E}",

year = "2006",

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AU - Phillips, David J

AU - Pillinger, Kathryn S

AU - Li, Wei

AU - Taylor, Angela E

AU - Graham, Andrew E

PY - 2006/6/4

Y1 - 2006/6/4

N2 - Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.

AB - Diols are desymmetrized by a tandem oxidation/Wittig olefination to give alpha,beta-unsaturated hydroxy esters without the requirement for protecting group strategies; the alpha,beta-unsaturated hydroxy esters are transformed into dienyl diesters using a second oxidation/Wittig olefination sequence using PCC.

KW - Alkenes

KW - Butylene Glycols

KW - Chemistry, Organic

KW - Esters

KW - Manganese Compounds

KW - Organic Chemistry Phenomena

KW - Oxidation-Reduction

KW - Oxides

KW - Stereoisomerism

U2 - 10.1039/b602329k

DO - 10.1039/b602329k

M3 - Article

C2 - 16718329

SN - 1359-7345

SP - 2280

EP - 2282

JO - Chemical Communications

JF - Chemical Communications

IS - 21

ER -

Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction

Abstract

Keywords

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