Iridium-Catalyzed Enantioselective Hydrogenation of Terminal Alkenes
Iridium complexes derived from chiral P,N ligands are efficient catalysts for the enantioselective hydrogenation of 2‐aryl‐substituted terminal alkenes. Using 0.1–1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88–94% ee), full conversions after shor...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2005-02, Vol.347 (2-3), p.282-288 |
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| container_title | Advanced synthesis & catalysis |
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| creator | McIntyre, Steven Hörmann, Esther Menges, Frederik Smidt, Sebastian P. Pfaltz, Andreas |
| description | Iridium complexes derived from chiral P,N ligands are efficient catalysts for the enantioselective hydrogenation of 2‐aryl‐substituted terminal alkenes. Using 0.1–1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88–94% ee), full conversions after short reaction times and essentially quantitative yields were obtained for a range of differently substituted 2‐arylalkenes. Among six iridium complexes that were tested, the most selective catalyst was a complex with a phosphinite‐oxazoline ligand derived from threonine (Ir‐ThrePHOX). In contrast to the hydrogenation of trisubstituted alkenes, a strong pressure effect was observed for this class of substrates. Lowering the hydrogen pressure from 50 to 1 bar resulted in a strong increase of the ee values. |
| doi_str_mv | 10.1002/adsc.200404256 |
| format | Article |
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Using 0.1–1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88–94% ee), full conversions after short reaction times and essentially quantitative yields were obtained for a range of differently substituted 2‐arylalkenes. Among six iridium complexes that were tested, the most selective catalyst was a complex with a phosphinite‐oxazoline ligand derived from threonine (Ir‐ThrePHOX). In contrast to the hydrogenation of trisubstituted alkenes, a strong pressure effect was observed for this class of substrates. Lowering the hydrogen pressure from 50 to 1 bar resulted in a strong increase of the ee values.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.200404256</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkenes ; asymmetric hydrogenation ; iridium ; N ligands ; oxazolines ; P,N ligands</subject><ispartof>Advanced synthesis & catalysis, 2005-02, Vol.347 (2-3), p.282-288</ispartof><rights>Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. 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Synth. Catal</addtitle><description>Iridium complexes derived from chiral P,N ligands are efficient catalysts for the enantioselective hydrogenation of 2‐aryl‐substituted terminal alkenes. Using 0.1–1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88–94% ee), full conversions after short reaction times and essentially quantitative yields were obtained for a range of differently substituted 2‐arylalkenes. Among six iridium complexes that were tested, the most selective catalyst was a complex with a phosphinite‐oxazoline ligand derived from threonine (Ir‐ThrePHOX). In contrast to the hydrogenation of trisubstituted alkenes, a strong pressure effect was observed for this class of substrates. Lowering the hydrogen pressure from 50 to 1 bar resulted in a strong increase of the ee values.</description><subject>alkenes</subject><subject>asymmetric hydrogenation</subject><subject>iridium</subject><subject>N ligands</subject><subject>oxazolines</subject><subject>P,N ligands</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRS0EEqWwZZ0fSBk7sZ0sq7TQShUIUQQ7y7XHyDRNkB0e4etpVVSxYzVXo3vu4hBySWFEAdiVttGMGEAOOePiiAyooDzNqSiPD5nDKTmL8RWAykLKAZnMg7f-fZNWutN1_402mTa66XwbsUbT-Q9MZr0N7Qs2evttktYlSwwb3-g6GddrbDCekxOn64gXv3dIHq-ny2qWLu5u5tV4kZpMSJGumGDa0sLlVorM6ZLJMneSZzzHggItROm4BmekKRjaUqDlDKi2K2AGDMuGZLTfNaGNMaBTb8FvdOgVBbVzoHYO1MHBFij3wKevsf-nrcaTh-ovm-5ZHzv8OrA6rJWQmeTq6fZGPS9FWVSMqfvsB5pDb9I</recordid><startdate>200502</startdate><enddate>200502</enddate><creator>McIntyre, Steven</creator><creator>Hörmann, Esther</creator><creator>Menges, Frederik</creator><creator>Smidt, Sebastian P.</creator><creator>Pfaltz, Andreas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200502</creationdate><title>Iridium-Catalyzed Enantioselective Hydrogenation of Terminal Alkenes</title><author>McIntyre, Steven ; Hörmann, Esther ; Menges, Frederik ; Smidt, Sebastian P. ; Pfaltz, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3676-b262ad18f4d763fa92794f75354e8101869f5a0fc7c82ed96ed5201adb02c0c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>alkenes</topic><topic>asymmetric hydrogenation</topic><topic>iridium</topic><topic>N ligands</topic><topic>oxazolines</topic><topic>P,N ligands</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McIntyre, Steven</creatorcontrib><creatorcontrib>Hörmann, Esther</creatorcontrib><creatorcontrib>Menges, Frederik</creatorcontrib><creatorcontrib>Smidt, Sebastian P.</creatorcontrib><creatorcontrib>Pfaltz, Andreas</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McIntyre, Steven</au><au>Hörmann, Esther</au><au>Menges, Frederik</au><au>Smidt, Sebastian P.</au><au>Pfaltz, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iridium-Catalyzed Enantioselective Hydrogenation of Terminal Alkenes</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2005-02</date><risdate>2005</risdate><volume>347</volume><issue>2-3</issue><spage>282</spage><epage>288</epage><pages>282-288</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Iridium complexes derived from chiral P,N ligands are efficient catalysts for the enantioselective hydrogenation of 2‐aryl‐substituted terminal alkenes. Using 0.1–1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88–94% ee), full conversions after short reaction times and essentially quantitative yields were obtained for a range of differently substituted 2‐arylalkenes. Among six iridium complexes that were tested, the most selective catalyst was a complex with a phosphinite‐oxazoline ligand derived from threonine (Ir‐ThrePHOX). In contrast to the hydrogenation of trisubstituted alkenes, a strong pressure effect was observed for this class of substrates. Lowering the hydrogen pressure from 50 to 1 bar resulted in a strong increase of the ee values.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.200404256</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | alkenes asymmetric hydrogenation iridium N ligands oxazolines P,N ligands |
| title | Iridium-Catalyzed Enantioselective Hydrogenation of Terminal Alkenes |
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