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: GrahamAEcardiff.ac.uk
D. J. Phillips, A. E. Graham, Synlett, 2010, 769-773.
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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guanidine bases, in situ ylide generation, Corey-Chaykovsky epoxidation, epoxides, enolizable aldehydes