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Organocatalytic asymmetric synthesis of dihydrofuran-spirooxindoles from benzylidene malononitriles and dioxindoles.
Org Biomol Chem
July 2019
Department of Chemistry, Indian Institute of Technology, Guwahati, 781039, India.
The first organocatalytic enantioselective synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position of the dihydrofuran motif has been developed. Dioxindoles and benzylidene malononitriles were employed in this method. The desired spirooxindole products were obtained via a Michael reaction followed by a Pinner reaction and isomerization and good to high yields with moderate diastereo and good to high enantioselectivities were observed.
View Article and Find Full Text PDFOrganocatalytic Asymmetric Synthesis of Bridged Acetals with Spirooxindole Skeleton.
J Org Chem
December 2018
Department of Chemistry , Indian Institute of Technology Guwahati, North Guwahati , Assam 781039 , India.
The first highly diastereo- and enantioselective synthesis of bridged O, O-acetals embedded with spirooxindoles has been developed. Dioxindoles and 2-hydroxy cinnamaldehydes were employed as the reaction partners in this method. The desired products were obtained via diaryl prolinol TBS ether catalyzed Michael reaction followed by acetal formation with TFA.
View Article and Find Full Text PDFIridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-Allyl-3-hydroxyoxindoles.
Org Lett
October 2018
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University, 800 Dongchuan Road , Shanghai 200240 , People's Republic of China.
An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-allyl-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).
View Article and Find Full Text PDFDioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes.
Chem Commun (Camb)
April 2012
Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain.
The asymmetric Michael addition of dioxindoles to β-substituted nitroalkenes is reported. The bifunctional primary amine-thiourea A, by means of a non-covalent-based mode of catalysis, secures direct access to 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol.
View Article and Find Full Text PDFDioxindole in asymmetric catalytic synthesis: routes to enantioenriched 3-substituted 3-hydroxyoxindoles and the preparation of maremycin A.
Angew Chem Int Ed Engl
January 2012
ICIQ-Institute of Chemical Research of Catalonia, Avenida Països Catalans 16, 43007 Tarragona, Spain.
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