Synfacts 2009(12): 1322-1322  
DOI: 10.1055/s-0029-1218227
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Rh-Catalyzed Synthesis of 2-Amido-furans via Cyclopropenation of Ynamides

Contributor(s): Victor Snieckus, Cédric Schneider
H. Li, R. P. Hsung*
University of Wisconsin, Madison, USA
Further Information

Publication History

Publication Date:
20 November 2009 (online)


Reported is the synthesis of 2-amido-furans 4 and 5 via a Rh(II) cyclopropenation of ynamides 1. Although the nature of intermediate (amido-cyclopropene or not) involved in this reaction is unknown, the 2-amido-furans 4 and 5 are clearly the result of a [3+2] cycloaddition process. After optimization, in particular the crucial identification of the best catalyst [Rh2(OAc)4], the desired 2-amido-furans were obtained in low to good yields even with sulfonyl- or terminally substituted ynamides. A clear trend is that the diazo compounds 2a,b are better cyclopropenating agents than iodonium ylides 3a,b. An application of these de novo 2-amido-furans in N-tethered intramolecular [4+2] cycloaddition is illustrated, leading to ­dihydroindoles 7 and tetrahydroquinolines 8.