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Development of Cationic Enantioselective Domino Carbopalladation/C(sp3)-Pd Capture Using N-Tosylhydrazones as Diazo
Vysakh Venugopalan Nair1, Karthikraja Esackraj2, Venkatesan Subramanian1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
Abstract:
The development of cationic enantioselective domino carbopalladation/C(sp3)-Pd capture using carbenes derived from N-tosylhydrazones to capture the enantioenriched alkyl-Pd species is reported. This method constructs a chiral quaternary carbon center and provides direct access to chiral 3,3-disubstituted oxindoles in yields up to 91% and >99% enantioselectivity with tolerance for diverse functional groups. The involved catalytic cycle and active catalytic species have been studied via mechanistic experiments, and a rationale for the observed stereochemical outcome has been proposed by DFT analysis.
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