Expedient access to substituted 3-amino-2-cyclopentenones by dirhodium-catalyzed [3+2]-annulation of silylated ketene imines and enoldiazoacetates.
In a reaction that proceeds under mild conditions with remarkable functional group tolerance, structurally diverse 3-amino-2-cyclopentenones bearing a quaternary carbon at the 4-position have been synthesized through a formal [3+2]-cycloaddition reaction of silylated ketene imines (SKIs) and enoldiazoaceates by dirhodium catalysis.
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20740, USA. mdoyle3@umd.edu.
Xichen
X
Xu
John S
JS
Leszczynski
Savannah M
SM
Mason
Peter Y
PY
Zavalij
Michael P
MP
Doyle
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003517:Cyclopentanes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
D000085:Acetates; D003517:Cyclopentanes; D003979:Diazonium Compounds; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D012238:Rhodium; C008223:ketene