Rh(III)-Catalyzed Relay Double Carbenoid Insertion and Diannulation of Sulfoximine Benzamides with α-Diazo Carbonyl Compounds: Access to Furo[2,3-<i>c</i>]isochromenes
Chen Yang, Chen Chen, LI Shun-fan, Xinwei He, Youpeng Zuo, Wangcheng Hu, Tongtong Zhou, Jian Wang, Yongjia Shang
Abstract
]isochromene scaffolds through tandem double carbenoid insertion and diannulation of sulfoximine benzamides with α-diazo carbonyl compounds has been developed. Mechanistic studies revealed that the alkyl-rhodium intermediate generated by carbenoid insertion was directly trapped with another molecule of carbene species, followed by subsequent intramolecular cyclization reactions. Sulfoximine was released in situ, featuring a traceless directing fashion. The reactions proceeded smoothly under mild conditions with wide functional group tolerance.
Topics & Concepts
ChemistryCarbenoidDiazoCatalysisMedicinal chemistryCombinatorial chemistryStereochemistryRhodiumOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions