Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.
Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.
Feltenberger
John B
JB
Department of Chemistry and Division of Pharmaceutical Sciences, University of Wisconsin, Madison, Wisconsin 53705, USA.
Hayashi
Ryuji
R
Tang
Yu
Y
Babiash
Eric S C
ES
Hsung
Richard P
RP
D000577:Amides / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; C524146:benzyne; D009584:Nitrogen