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

David J. Phillips, Andrew E. Graham

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


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 languageEnglish
Article numberD30409ST
Pages (from-to)769-773
Number of pages5
Issue number5
Publication statusPublished - 2010


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


Dive into the research topics of 'Guanidine bases in synthesis: Extending the scope of the corey-chaykovsky epoxidation'. Together they form a unique fingerprint.

Cite this