Unprecedented Halide Dependence on Catalytic Asymmetric Hydrogenation of 2‐Aryl‐ and 2‐Alkyl‐Substituted Quinolinium Salts by Using Ir Complexes with Difluorphos and Halide Ligands

A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of 2‐aryl‐ and 2‐alkyl‐substituted quinolinium salts. The reaction was catalyzed by a cationic dinuclear iridium(III) complex with difluorphos and...

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Published inChemistry : a European journal Vol. 15; no. 39; pp. 9990 - 9994
Main Authors Tadaoka, Hiroshi, Cartigny, Damien, Nagano, Takuto, Gosavi, Tushar, Ayad, Tahar, Genêt, Jean‐Pierre, Ohshima, Takashi, Ratovelomanana‐Vidal, Virginie, Mashima, Kazushi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag 05.10.2009
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Abstract A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of 2‐aryl‐ and 2‐alkyl‐substituted quinolinium salts. The reaction was catalyzed by a cationic dinuclear iridium(III) complex with difluorphos and chloride or bromide ligands and gave the corresponding 2‐substituted 1,2,3,4‐tetrahydroquinolines in high enantioselectivities (up to 95 % ee; see scheme, difluorphos=[(4,4′‐bi‐2,2‐difluoro‐1,3‐benzodioxole)‐5,5′‐diyl]bis(diphenylphosphine)).
AbstractList A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of 2‐aryl‐ and 2‐alkyl‐substituted quinolinium salts. The reaction was catalyzed by a cationic dinuclear iridium(III) complex with difluorphos and chloride or bromide ligands and gave the corresponding 2‐substituted 1,2,3,4‐tetrahydroquinolines in high enantioselectivities (up to 95 % ee; see scheme, difluorphos=[(4,4′‐bi‐2,2‐difluoro‐1,3‐benzodioxole)‐5,5′‐diyl]bis(diphenylphosphine)).
Author Ohshima, Takashi
Nagano, Takuto
Cartigny, Damien
Ratovelomanana‐Vidal, Virginie
Gosavi, Tushar
Genêt, Jean‐Pierre
Ayad, Tahar
Mashima, Kazushi
Tadaoka, Hiroshi
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  surname: Tadaoka
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  givenname: Damien
  surname: Cartigny
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  givenname: Takuto
  surname: Nagano
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  surname: Gosavi
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  givenname: Tahar
  surname: Ayad
  fullname: Ayad, Tahar
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  givenname: Jean‐Pierre
  surname: Genêt
  fullname: Genêt, Jean‐Pierre
– sequence: 7
  givenname: Takashi
  surname: Ohshima
  fullname: Ohshima, Takashi
  email: ohshima@chem.es.osaka‐u.ac.jp
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  givenname: Kazushi
  surname: Mashima
  fullname: Mashima, Kazushi
  email: mashima@chem.es.osaka‐u.ac.jp
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Issue 39
Keywords BETA-HYDROXY ESTERS
STEREOSELECTIVE HYDROGENATION
HETEROAROMATIC-COMPOUNDS
ACYCLIC IMINES
iridium
HIGHLY ENANTIOSELECTIVE HYDROGENATION
asymmetric synthesis
IRIDIUM COMPLEXES
ENHANCEMENT
SYNTHETIC APPLICATIONS
enantioselectivity hydrogenation
quinolines
CYCLIC IMINES
METOLACHLOR
Language English
License Distributed under a Creative Commons Attribution 4.0 International License: http://creativecommons.org/licenses/by/4.0
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Wiley
Wiley-VCH Verlag
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Snippet A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of...
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SubjectTerms asymmetric synthesis
Chemistry
Chemistry, Multidisciplinary
enantioselectivity
hydrogenation
iridium
Physical Sciences
quinolines
Science & Technology
Title Unprecedented Halide Dependence on Catalytic Asymmetric Hydrogenation of 2‐Aryl‐ and 2‐Alkyl‐Substituted Quinolinium Salts by Using Ir Complexes with Difluorphos and Halide Ligands
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.200901477
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Volume 15
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