Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

Linglin Wu; Laura Falivene; Emma E. Drinkel; Sharday Grant; Anthony Linden; Luigi Cavallo; Reto Dorta

doi:10.1002/anie.201200206

Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

Linglin Wu, Laura Falivene, Emma E. Drinkel, Sharday Grant, Anthony Linden, Luigi Cavallo, Reto Dorta

Research output: Contribution to journal › Article › peer-review

125 Scopus citations

Abstract

Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	2870-2873
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	51
Issue number	12
DOIs	https://doi.org/10.1002/anie.201200206
State	Published - Feb 6 2012

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KAUST Repository Item: Exported on 2020-10-01

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201200206

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abstract = "Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright {\textcopyright} 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Linglin Wu and Laura Falivene and Drinkel, {Emma E.} and Sharday Grant and Anthony Linden and Luigi Cavallo and Reto Dorta",

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T1 - Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

AU - Wu, Linglin

AU - Falivene, Laura

AU - Drinkel, Emma E.

AU - Grant, Sharday

AU - Linden, Anthony

AU - Cavallo, Luigi

AU - Dorta, Reto

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2012/2/6

Y1 - 2012/2/6

N2 - Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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UR - http://doi.wiley.com/10.1002/anie.201200206

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 12

ER -

Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

Abstract

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CCDC 861318: Experimental Crystal Structure Determination : (R~a~,R~a~)-3-Fluoro-3-(3-fluorophenyl)-1-methyl-1,3-dihydro-2H-indol-2-one

CCDC 861317: Experimental Crystal Structure Determination : (S)-(eta^3^-1-phenylprop-1-en-3-yl)-(1,3-bis(2-cyclooctylnaphthalen-1-yl)-4,5-diphenylimidazolidin-2-ylidene)-chloro-palladium ethyl acetate solvate

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Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 861318: Experimental Crystal Structure Determination : (R~a~,R~a~)-3-Fluoro-3-(3-fluorophenyl)-1-methyl-1,3-dihydro-2H-indol-2-one

CCDC 861317: Experimental Crystal Structure Determination : (S)-(eta^3^-1-phenylprop-1-en-3-yl)-(1,3-bis(2-cyclooctylnaphthalen-1-yl)-4,5-diphenylimidazolidin-2-ylidene)-chloro-palladium ethyl acetate solvate

Cite this