In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols

David J. Phillips; Andrew E. Graham

doi:10.1055/s-2008-1042799

In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols

David J. Phillips, Andrew E. Graham

Faculty of Computing, Engineering and Science

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

17 Citations (Scopus)

Abstract

An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields.

Original language	English
Pages (from-to)	649-652
Number of pages	4
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-2008-1042799
Publication status	Published - 18 Mar 2008

Keywords

α,β-unsaturated hydroxy esters
Diol desymmetrization
In situ ylide generation
Lactone formation

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10.1055/s-2008-1042799Licence: CC BY-NC-ND

17 Citations
1 Doctoral Thesis

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors
Phillips, D., 2007
Research output: Types of Thesis › Doctoral Thesis

Cite this

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title = "In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols",

abstract = "An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields. ",

keywords = "α,β-unsaturated hydroxy esters, Diol desymmetrization, In situ ylide generation, Lactone formation",

author = "Phillips, {David J.} and Graham, {Andrew E.}",

year = "2008",

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AU - Phillips, David J.

AU - Graham, Andrew E.

PY - 2008/3/18

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N2 - An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields.

AB - An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields.

KW - α,β-unsaturated hydroxy esters

KW - Diol desymmetrization

KW - In situ ylide generation

KW - Lactone formation

U2 - 10.1055/s-2008-1042799

DO - 10.1055/s-2008-1042799

M3 - Article

AN - SCOPUS:41349106225

SN - 0936-5214

SP - 649

EP - 652

JO - Synlett

JF - Synlett

IS - 5

ER -

In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols

Abstract

Keywords

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Research output

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors

Cite this