title: Highly Regio- and Enantioselective Formal [3 + 2]-Annulation of Indoles with Electrophilic Enol Carbene Intermediates.
abstract: Chiral cyclopentane-fused indolines are synthesized with high regio- and enantiocontrol by formal [3 + 2]-annulation reactions of indoles and electrophilic enol carbenes. High enantioselectivity and exclusive regiocontrol occurred with enoldiazoacetamides using a less sterically encumbered prolinate-ligated dirhodium(II) catalyst in reactions with N-substituted indoles without substituents at the 2- or 3-positions via a selective vinylogous addition process. In this transformation, donor-acceptor cyclopropenes generated from enoldiazoacetamides serve as the carbene precursors to form metal carbene intermediates.
authors: Shanghai Engineering Research Centre of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , Shanghai 200062, P.R. China.
authors: Changcheng
authors: C
authors: Jing
authors: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors: Qing-Qing
authors: QQ
authors: Cheng
authors: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors: Yongming
authors: Y
authors: Deng
authors: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors: Hadi
authors: H
authors: Arman
authors: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors: Michael P
authors: MP
authors: Doyle