ol0c00587_si_001.pdf (3.6 MB)
Brønsted Acid Catalyzed Enantioselective Assembly of Spirochroman-3,3-oxindoles
journal contribution
posted on 2020-04-01, 18:33 authored by Alavala Gopi Krishna Reddy, Pedireddi Niharika, Su Zhou, Shi-Kun Jia, Taoda Shi, Xinfang Xu, Yu Qian, Wenhao HuAn enantioselective
cyclization of diazoindolinones with o-hydroxymethyl
chalcones has been established by a cooperative
dirhodium complex and chiral phosphonic acid catalysis under mild
conditions. This reaction is the first example of catalytic asymmetric
intramolecular Michael-type trapping of oxonium ylide enabled by phosphoric
acid through a dual H-bonding activation model, which provides an
efficient access to the chiral spirochroman-3,3-oxindoles, with vicinal
quaternary and tertiary stereocenters, in good to excellent yields
and enantioselectivities.
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chiral phosphonic acid catalysisphosphoric acidSpirochromanBr ønstedintramolecular Michael-typeaccessspirochromanenantioselectivitiestereocenterhydroxymethyl chalconesoxonium ylideenantioselective cyclizationvicinal quaternarydiazoindolinoneyieldH-bonding activation modelCatalyzed Enantioselective Assemblydirhodium
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