A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts
A series of chiral proline amide – thiourea bifunctional catalysts derived from l -proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/s...
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| Veröffentlicht in: | Canadian journal of chemistry 2011-11, Vol.89 (10), p.1312-1318 |
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| container_end_page | 1318 |
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| container_issue | 10 |
| container_start_page | 1312 |
| container_title | Canadian journal of chemistry |
| container_volume | 89 |
| creator | Li, Yun Yang, Qing-chuan Xu, Xiao-Ying Zhou, Yong Bai, Jian-fei Wang, Fei- ying Wang, Li-xin |
| description | A series of chiral proline amide – thiourea bifunctional catalysts derived from
l
-proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/syn > 20:1) and enantioselectivities (up to 91% ee). |
| doi_str_mv | 10.1139/v11-029 |
| format | Article |
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l
-proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/syn > 20:1) and enantioselectivities (up to 91% ee).</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v11-029</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa: NRC Research Press</publisher><subject>Aldehydes ; aldol reaction ; amide–thiourea ; amide–thiourée ; bifunctional catalyst ; catalyseur bifonctionnel ; Catalysts ; Chemical reactions ; Cyclohexanone ; Diamines ; Enantiomers ; Organosulfur compounds ; Proline ; réaction aldolique ; Thioureas</subject><ispartof>Canadian journal of chemistry, 2011-11, Vol.89 (10), p.1312-1318</ispartof><rights>COPYRIGHT 2011 NRC Research Press</rights><rights>2011 Published by NRC Research Press</rights><rights>Copyright National Research Council of Canada Oct 2011</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c546t-3dbb10cad6d11da6a0671531cbc793d65ba57b4a41d60591df826ce6e558fe323</citedby><cites>FETCH-LOGICAL-c546t-3dbb10cad6d11da6a0671531cbc793d65ba57b4a41d60591df826ce6e558fe323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Li, Yun</creatorcontrib><creatorcontrib>Yang, Qing-chuan</creatorcontrib><creatorcontrib>Xu, Xiao-Ying</creatorcontrib><creatorcontrib>Zhou, Yong</creatorcontrib><creatorcontrib>Bai, Jian-fei</creatorcontrib><creatorcontrib>Wang, Fei- ying</creatorcontrib><creatorcontrib>Wang, Li-xin</creatorcontrib><title>A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts</title><title>Canadian journal of chemistry</title><description>A series of chiral proline amide – thiourea bifunctional catalysts derived from
l
-proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/syn > 20:1) and enantioselectivities (up to 91% ee).</description><subject>Aldehydes</subject><subject>aldol reaction</subject><subject>amide–thiourea</subject><subject>amide–thiourée</subject><subject>bifunctional catalyst</subject><subject>catalyseur bifonctionnel</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Cyclohexanone</subject><subject>Diamines</subject><subject>Enantiomers</subject><subject>Organosulfur compounds</subject><subject>Proline</subject><subject>réaction aldolique</subject><subject>Thioureas</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqV0ltrFDEUB_AgFlyr-BVCBUVhapLJZeZxKWoLpYKX55BJzuykzGWbZMXxqa8--w37SRrdgi5sBQkkJPz-h0M4CD2j5JjSsn7zldKCsPoBWlBekaJkNX2IFoSQquCEs0focYyX-aoIEwsUl7jzq66fsYnzMEAK3mLnA9iETe-mHgcwNvlpxNYk08_fweFmxrbzwfR4Habej4DN4B3cXP-4uf6Z99T5aZNzuPHtZvydznabjyk-QQet6SM8vTsP0Zd3bz-fnBbnH96fnSzPCyu4TEXpmoYSa5x0lDojDZGKipLaxqq6dFI0RqiGG06dJKKmrq2YtCBBiKqFkpWH6GhbN3d5tYGY9GVuK7cSdVUrroSqeUbP70OMs7Liggn1R61MD9qP7ZSCsYOPVi-ZYlQqxausij1qBSPkv5pGaH1-3vFHe7xd-yv9Nzreg_JyMHi7t-qrnUA2Cb6lldnEqM8-ffwPe7FrX26tDVOMAVq9Dn4wYdaU6F-jp_Po6Tx6Wb7eyjHYABFMsN0_8Iv78R3Sa9eWtzpO5eQ</recordid><startdate>20111101</startdate><enddate>20111101</enddate><creator>Li, Yun</creator><creator>Yang, Qing-chuan</creator><creator>Xu, Xiao-Ying</creator><creator>Zhou, Yong</creator><creator>Bai, Jian-fei</creator><creator>Wang, Fei- ying</creator><creator>Wang, Li-xin</creator><general>NRC Research Press</general><general>Canadian Science Publishing NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISN</scope><scope>ISR</scope></search><sort><creationdate>20111101</creationdate><title>A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts</title><author>Li, Yun ; Yang, Qing-chuan ; Xu, Xiao-Ying ; Zhou, Yong ; Bai, Jian-fei ; Wang, Fei- ying ; Wang, Li-xin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c546t-3dbb10cad6d11da6a0671531cbc793d65ba57b4a41d60591df826ce6e558fe323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aldehydes</topic><topic>aldol reaction</topic><topic>amide–thiourea</topic><topic>amide–thiourée</topic><topic>bifunctional catalyst</topic><topic>catalyseur bifonctionnel</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Cyclohexanone</topic><topic>Diamines</topic><topic>Enantiomers</topic><topic>Organosulfur compounds</topic><topic>Proline</topic><topic>réaction aldolique</topic><topic>Thioureas</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Yun</creatorcontrib><creatorcontrib>Yang, Qing-chuan</creatorcontrib><creatorcontrib>Xu, Xiao-Ying</creatorcontrib><creatorcontrib>Zhou, Yong</creatorcontrib><creatorcontrib>Bai, Jian-fei</creatorcontrib><creatorcontrib>Wang, Fei- ying</creatorcontrib><creatorcontrib>Wang, Li-xin</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Canada</collection><collection>Gale In Context: Science</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Yun</au><au>Yang, Qing-chuan</au><au>Xu, Xiao-Ying</au><au>Zhou, Yong</au><au>Bai, Jian-fei</au><au>Wang, Fei- ying</au><au>Wang, Li-xin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts</atitle><jtitle>Canadian journal of chemistry</jtitle><date>2011-11-01</date><risdate>2011</risdate><volume>89</volume><issue>10</issue><spage>1312</spage><epage>1318</epage><pages>1312-1318</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>A series of chiral proline amide – thiourea bifunctional catalysts derived from
l
-proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/syn > 20:1) and enantioselectivities (up to 91% ee).</abstract><cop>Ottawa</cop><pub>NRC Research Press</pub><doi>10.1139/v11-029</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 2011-11, Vol.89 (10), p.1312-1318 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_proquest_journals_2423845257 |
| source | Free Full-Text Journals in Chemistry |
| subjects | Aldehydes aldol reaction amide–thiourea amide–thiourée bifunctional catalyst catalyseur bifonctionnel Catalysts Chemical reactions Cyclohexanone Diamines Enantiomers Organosulfur compounds Proline réaction aldolique Thioureas |
| title | A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts |
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