Guanidine bases in synthesis: Extending the scope of the corey-chaykovsky epoxidation

David J. Phillips; Andrew E. Graham

doi:10.1055/s-0029-1219359

Guanidine bases in synthesis: Extending the scope of the corey-chaykovsky epoxidation

David J. Phillips, Andrew E. Graham

Faculty of Computing, Engineering and Science

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

11 Citations (Scopus)

Abstract

Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.

Original language	English
Article number	D30409ST
Pages (from-to)	769-773
Number of pages	5
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-0029-1219359
Publication status	Published - 2010

Keywords

Corey-Chaykovsky epoxidation
Enolizable aldehydes
Epoxides
Guanidine bases
In situ ylide generation

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10.1055/s-0029-1219359Licence: CC BY-NC-ND

11 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 = "Guanidine bases in synthesis: Extending the scope of the corey-chaykovsky epoxidation",

abstract = "Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.",

keywords = "Corey-Chaykovsky epoxidation, Enolizable aldehydes, Epoxides, Guanidine bases, In situ ylide generation",

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

year = "2010",

doi = "10.1055/s-0029-1219359",

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T1 - Guanidine bases in synthesis

T2 - Extending the scope of the corey-chaykovsky epoxidation

AU - Phillips, David J.

AU - Graham, Andrew E.

PY - 2010

Y1 - 2010

N2 - Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.

AB - Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.

KW - Corey-Chaykovsky epoxidation

KW - Enolizable aldehydes

KW - Epoxides

KW - Guanidine bases

KW - In situ ylide generation

U2 - 10.1055/s-0029-1219359

DO - 10.1055/s-0029-1219359

M3 - Article

AN - SCOPUS:77749283853

SN - 0936-5214

SP - 769

EP - 773

JO - Synlett

JF - Synlett

IS - 5

M1 - D30409ST

ER -

Guanidine bases in synthesis: Extending the scope of the corey-chaykovsky epoxidation

Abstract

Keywords

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Research output

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

Cite this