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 in | Chemistry : a European journal Vol. 15; no. 39; pp. 9990 - 9994 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY‐VCH Verlag
05.10.2009
Wiley Wiley-VCH Verlag |
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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)). |
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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 |
Author_xml | – sequence: 1 givenname: Hiroshi surname: Tadaoka fullname: Tadaoka, Hiroshi – sequence: 2 givenname: Damien surname: Cartigny fullname: Cartigny, Damien – sequence: 3 givenname: Takuto surname: Nagano fullname: Nagano, Takuto – sequence: 4 givenname: Tushar surname: Gosavi fullname: Gosavi, Tushar – sequence: 5 givenname: Tahar surname: Ayad fullname: Ayad, Tahar – sequence: 6 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 – sequence: 8 givenname: Virginie surname: Ratovelomanana‐Vidal fullname: Ratovelomanana‐Vidal, Virginie email: virginie‐vidal@enscp.fr – sequence: 9 givenname: Kazushi surname: Mashima fullname: Mashima, Kazushi email: mashima@chem.es.osaka‐u.ac.jp |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/19711392$$D View this record in MEDLINE/PubMed https://hal.science/hal-00449032$$DView record in HAL |
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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 |
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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... |
Source | Web of Science |
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StartPage | 9990 |
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 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000270854200005 https://www.ncbi.nlm.nih.gov/pubmed/19711392 https://search.proquest.com/docview/734071762 https://hal.science/hal-00449032 |
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