Yb(OTf)₃ catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

Abstract

A Yb(OTf)3 catalyzed [1,3]-rearrangement of 3- alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields and Z/E selectivities (64%-89% yield, 78:22->99:1 Z/E). Importantly, an operationally simple, one-pot sequential...

Organocatalytic Activation of Donor–Acceptor Cyclopropanes: A Tandem (3 + 3)-Cycloaddition/Aryl Migration toward the Synthesis of Enantioenriched Tetrahydropyridazines

“…The rearranged products 3ab and 3ap were obtained in 26 and 24% yields, respectively, whereas no cross-rearrangement products were detected. This study disclosed that this unusual [1,3]-aryl shift proceeds via an intramolecular and concerted rearrangement pathway . Moreover, this aryl migration could happen either via Friedel–Crafts-type reaction or via ipso -type substitution.…”