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Guanidine Bases in Synthesis: Extending the Scope of the Corey-Chaykovsky Epoxidation

David J. Phillips, Andrew E. Graham*

*School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CA10 8PP, UK, Email:

D. J. Phillips, A. E. Graham, Synlett, 2010, 769-773.

DOI: 10.1055/s-0029-1219359


Guanidine bases are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky reactions of aldehydes to produce the corresponding epoxides in excellent yields and with high diastereoselectivity. Significantly, both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes can be converted.

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Key Words

guanidine bases, in situ ylide generation, Corey-Chaykovsky epoxidation, epoxides, enolizable aldehydes

ID: J60-Y2010-0680