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Synfacts 2009(5): 0485-0485
DOI: 10.1055/s-0029-1216601
DOI: 10.1055/s-0029-1216601
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Three-Component Synthesis of Di- and Tetrahydrofurans under Rhodium Catalysis
A. DeAngelis, M. T. Taylor, J. M. Fox*
University of Delaware, Newark, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)

Significance
The rhodium-catalyzed synthesis of highly functionalized di- and tetrahydrofurans is reported via the three-component coupling of aldehydes, α-alkyl-α-diazoesters and dipolarophiles. The α-alkyl carbonyl ylides formed in situ are highly reactive towards dipolarophiles, offering the desired products in high yield and demonstrate broad substrate scope compared to unsubstituted or α-aryldiazoacetates. The reaction proceeds with excellent regio- and stereoselectivity in nearly all cases, which is rationalized by an asynchronous endo transition state.