Dabbling with air-stable organoaluminum species
Highly stereoselective 1,2-additions of AlMe or its air-stable analog DABCO(AlMe to aldehydes are realized in the presence of a Ni(acac) -derived catalyst using phosphoramidite ligands giving -alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350...
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| Veröffentlicht in: | Pure and applied chemistry 2006-02, Vol.78 (2), p.511-518 |
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| container_title | Pure and applied chemistry |
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| creator | Biswas, Kallolmay Chapron, Alex Cooper, Thea Fraser, Paul K. Novak, Andrew Prieto, Oscar Woodward, Simon |
| description | Highly stereoselective 1,2-additions of AlMe
or its air-stable analog DABCO(AlMe
to aldehydes are realized in the presence of a Ni(acac)
-derived catalyst using phosphoramidite ligands giving
-alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350 h
) values can be realized in these reactions. The substrate range, trials of various (DABCO)
(AlR
reagents (
= 0.1;
= 1.2; R = Me, Et, Bu
), ligands, and molecular modeling studies are used to propose a working model for the catalytic cycle and the origin of the stereoselectivity. The phosphoramidite ligand is proposed to bind the nickel in an η
manner via the
-donor and one of the C=C aryl bonds of the CHAr amine group. Preliminary studies indicate that DABCO(AlMe
can also be used as a methyl source in Pd-catalyzed cross-coupling reactions of ArX (X = Br, I) species. |
| doi_str_mv | 10.1351/pac200678020511 |
| format | Article |
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or its air-stable analog DABCO(AlMe
to aldehydes are realized in the presence of a Ni(acac)
-derived catalyst using phosphoramidite ligands giving
-alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350 h
) values can be realized in these reactions. The substrate range, trials of various (DABCO)
(AlR
reagents (
= 0.1;
= 1.2; R = Me, Et, Bu
), ligands, and molecular modeling studies are used to propose a working model for the catalytic cycle and the origin of the stereoselectivity. The phosphoramidite ligand is proposed to bind the nickel in an η
manner via the
-donor and one of the C=C aryl bonds of the CHAr amine group. Preliminary studies indicate that DABCO(AlMe
can also be used as a methyl source in Pd-catalyzed cross-coupling reactions of ArX (X = Br, I) species.</description><identifier>ISSN: 0033-4545</identifier><identifier>EISSN: 1365-3075</identifier><identifier>DOI: 10.1351/pac200678020511</identifier><language>eng</language><publisher>Berlin: De Gruyter</publisher><subject>1,2-additions ; Alcohols ; Aldehydes ; Aromatic compounds ; asymmetric synthesis ; Catalysis ; catalytic asymmetric synthesis ; Chemical reactions ; Coupling (molecular) ; Cross coupling ; DABCO(AlMe3)2 ; Ligands ; Nickel ; Reagents ; stereoselective ; Stereoselectivity ; Substrates ; trimethylaluminum</subject><ispartof>Pure and applied chemistry, 2006-02, Vol.78 (2), p.511-518</ispartof><rights>2013 Walter de Gruyter GmbH, Berlin/Boston</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c364t-86b8f3b8353e9998aad11b222d066584bebde896a7afd2bf52866d9fb29868f83</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Biswas, Kallolmay</creatorcontrib><creatorcontrib>Chapron, Alex</creatorcontrib><creatorcontrib>Cooper, Thea</creatorcontrib><creatorcontrib>Fraser, Paul K.</creatorcontrib><creatorcontrib>Novak, Andrew</creatorcontrib><creatorcontrib>Prieto, Oscar</creatorcontrib><creatorcontrib>Woodward, Simon</creatorcontrib><title>Dabbling with air-stable organoaluminum species</title><title>Pure and applied chemistry</title><description>Highly stereoselective 1,2-additions of AlMe
or its air-stable analog DABCO(AlMe
to aldehydes are realized in the presence of a Ni(acac)
-derived catalyst using phosphoramidite ligands giving
-alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350 h
) values can be realized in these reactions. The substrate range, trials of various (DABCO)
(AlR
reagents (
= 0.1;
= 1.2; R = Me, Et, Bu
), ligands, and molecular modeling studies are used to propose a working model for the catalytic cycle and the origin of the stereoselectivity. The phosphoramidite ligand is proposed to bind the nickel in an η
manner via the
-donor and one of the C=C aryl bonds of the CHAr amine group. Preliminary studies indicate that DABCO(AlMe
can also be used as a methyl source in Pd-catalyzed cross-coupling reactions of ArX (X = Br, I) species.</description><subject>1,2-additions</subject><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Aromatic compounds</subject><subject>asymmetric synthesis</subject><subject>Catalysis</subject><subject>catalytic asymmetric synthesis</subject><subject>Chemical reactions</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>DABCO(AlMe3)2</subject><subject>Ligands</subject><subject>Nickel</subject><subject>Reagents</subject><subject>stereoselective</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>trimethylaluminum</subject><issn>0033-4545</issn><issn>1365-3075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp1kMtLw0AYxBdRsFbPXgOeY799ZvfgQeoTCl70HL5NdmNKXu4mlP73plQQBE8zh_nNwBByTeGWcklXAxYMQGUaGEhKT8iCciVTDpk8JQsAzlMhhTwnFzFuAUAYwRZk9YDWNnVXJbt6_EywDmkc0TYu6UOFXY_N1Nbd1CZxcEXt4iU589hEd_WjS_Lx9Pi-fkk3b8-v6_tNWnAlxlQrqz23mkvujDEasaTUMsZKUEpqYZ0tnTYKM_Qls14yrVRpvGVGK-01X5KbY-8Q-q_JxTHf9lPo5smcMQ5UZyDEnFodU0XoYwzO50OoWwz7nEJ-eCX_88pM3B2JHTajC6WrwrSfzW_9P2Sm2YH_Bl93Z3M</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Biswas, Kallolmay</creator><creator>Chapron, Alex</creator><creator>Cooper, Thea</creator><creator>Fraser, Paul K.</creator><creator>Novak, Andrew</creator><creator>Prieto, Oscar</creator><creator>Woodward, Simon</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope></search><sort><creationdate>20060201</creationdate><title>Dabbling with air-stable organoaluminum species</title><author>Biswas, Kallolmay ; Chapron, Alex ; Cooper, Thea ; Fraser, Paul K. ; Novak, Andrew ; Prieto, Oscar ; Woodward, Simon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c364t-86b8f3b8353e9998aad11b222d066584bebde896a7afd2bf52866d9fb29868f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>1,2-additions</topic><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Aromatic compounds</topic><topic>asymmetric synthesis</topic><topic>Catalysis</topic><topic>catalytic asymmetric synthesis</topic><topic>Chemical reactions</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>DABCO(AlMe3)2</topic><topic>Ligands</topic><topic>Nickel</topic><topic>Reagents</topic><topic>stereoselective</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>trimethylaluminum</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Biswas, Kallolmay</creatorcontrib><creatorcontrib>Chapron, Alex</creatorcontrib><creatorcontrib>Cooper, Thea</creatorcontrib><creatorcontrib>Fraser, Paul K.</creatorcontrib><creatorcontrib>Novak, Andrew</creatorcontrib><creatorcontrib>Prieto, Oscar</creatorcontrib><creatorcontrib>Woodward, Simon</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Pure and applied chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Biswas, Kallolmay</au><au>Chapron, Alex</au><au>Cooper, Thea</au><au>Fraser, Paul K.</au><au>Novak, Andrew</au><au>Prieto, Oscar</au><au>Woodward, Simon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dabbling with air-stable organoaluminum species</atitle><jtitle>Pure and applied chemistry</jtitle><date>2006-02-01</date><risdate>2006</risdate><volume>78</volume><issue>2</issue><spage>511</spage><epage>518</epage><pages>511-518</pages><issn>0033-4545</issn><eissn>1365-3075</eissn><abstract>Highly stereoselective 1,2-additions of AlMe
or its air-stable analog DABCO(AlMe
to aldehydes are realized in the presence of a Ni(acac)
-derived catalyst using phosphoramidite ligands giving
-alcohols in up to 95 % ee. Very high turnover number (TON) (>1500) and turnover frequency (TOF) (>350 h
) values can be realized in these reactions. The substrate range, trials of various (DABCO)
(AlR
reagents (
= 0.1;
= 1.2; R = Me, Et, Bu
), ligands, and molecular modeling studies are used to propose a working model for the catalytic cycle and the origin of the stereoselectivity. The phosphoramidite ligand is proposed to bind the nickel in an η
manner via the
-donor and one of the C=C aryl bonds of the CHAr amine group. Preliminary studies indicate that DABCO(AlMe
can also be used as a methyl source in Pd-catalyzed cross-coupling reactions of ArX (X = Br, I) species.</abstract><cop>Berlin</cop><pub>De Gruyter</pub><doi>10.1351/pac200678020511</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Pure and applied chemistry, 2006-02, Vol.78 (2), p.511-518 |
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| language | eng |
| recordid | cdi_proquest_journals_2230187044 |
| source | EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 1,2-additions Alcohols Aldehydes Aromatic compounds asymmetric synthesis Catalysis catalytic asymmetric synthesis Chemical reactions Coupling (molecular) Cross coupling DABCO(AlMe3)2 Ligands Nickel Reagents stereoselective Stereoselectivity Substrates trimethylaluminum |
| title | Dabbling with air-stable organoaluminum species |
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