Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.
Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-furans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-furans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.
Li
Hongyan
H
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Hsung
Richard P
RP
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D003521:Cyclopropanes; D005663:Furans; D009942:Organometallic Compounds; D012238:Rhodium