Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes
The active catalysts for the enantioselective ring opening (ARO) of meso‐stilbene oxide, cis‐butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(OiPr)4 with poly‐[(R,R)‐N,N′‐bis‐{3‐(1,1‐dimethylethy...
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Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2011-01, Vol.23 (1), p.76-83 |
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description | The active catalysts for the enantioselective ring opening (ARO) of meso‐stilbene oxide, cis‐butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(OiPr)4 with poly‐[(R,R)‐N,N′‐bis‐{3‐(1,1‐dimethylethyl)‐5‐methylene salicylidene} cyclohexane‐1,2‐diamine]‐1 and (1R,2R)‐N,N′‐bis[3,5‐di(tert‐butyl)salicylidene] cyclohexane‐1,2‐diamine‐2. These catalysts in the presence of nonracemic imine as an additive provided β‐amino alcohol in excellent yield (99%) and chiral purity (enantiomeric excess (ee) up to 99%) for the ARO of meso‐stilbene oxide with aniline. The same protocol was less effective for the ARO of cyclic epoxides; however, when triphenylphosphine was used as an additive, there was a significant improvement in catalyst performance for the ARO of cyclohexene oxide (yield, 85–90%; ee, 63–67%). Both in situ generated polymeric and monomeric catalysts performed in a similar manner except that the polymeric catalyst Ti(IV)‐1 was more active and recycled several times with retention of enantioselectivity when compared with the monomeric catalyst Ti(IV)‐2, which was nonrecyclable. Chirality, 2011. © 2010 Wiley‐Liss, Inc. |
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R. ; Bajaj, Hari C.</creator><creatorcontrib>Kureshy, Rukhsana I. ; Kumar, Manish ; Agrawal, Santosh ; Khan, Noor-Ul H. ; Dangi, Balchand ; Abdi, Sayed H. R. ; Bajaj, Hari C.</creatorcontrib><description>The active catalysts for the enantioselective ring opening (ARO) of meso‐stilbene oxide, cis‐butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(OiPr)4 with poly‐[(R,R)‐N,N′‐bis‐{3‐(1,1‐dimethylethyl)‐5‐methylene salicylidene} cyclohexane‐1,2‐diamine]‐1 and (1R,2R)‐N,N′‐bis[3,5‐di(tert‐butyl)salicylidene] cyclohexane‐1,2‐diamine‐2. These catalysts in the presence of nonracemic imine as an additive provided β‐amino alcohol in excellent yield (99%) and chiral purity (enantiomeric excess (ee) up to 99%) for the ARO of meso‐stilbene oxide with aniline. The same protocol was less effective for the ARO of cyclic epoxides; however, when triphenylphosphine was used as an additive, there was a significant improvement in catalyst performance for the ARO of cyclohexene oxide (yield, 85–90%; ee, 63–67%). Both in situ generated polymeric and monomeric catalysts performed in a similar manner except that the polymeric catalyst Ti(IV)‐1 was more active and recycled several times with retention of enantioselectivity when compared with the monomeric catalyst Ti(IV)‐2, which was nonrecyclable. Chirality, 2011. © 2010 Wiley‐Liss, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>ISSN: 1520-636X</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.20868</identifier><identifier>PMID: 21125689</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc., A Wiley Company</publisher><subject>Additives ; Aniline ; Catalysis ; Catalysts ; chiral monomeric and polymeric Ti(IV) ; Chirality ; Cyclohexene ; enantioselective ring opening ; meso-epoxides ; Oxides ; Recycled ; salen ; syn and anti-β-aminoalcohol</subject><ispartof>Chirality (New York, N.Y.), 2011-01, Vol.23 (1), p.76-83</ispartof><rights>Copyright © 2010 Wiley‐Liss, Inc.</rights><rights>Copyright © 2010 Wiley-Liss, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4328-dc6ae913e39518a0a8f5bb4c9a89aca4435af93eabed419386e526c769b14aac3</citedby><cites>FETCH-LOGICAL-c4328-dc6ae913e39518a0a8f5bb4c9a89aca4435af93eabed419386e526c769b14aac3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.20868$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.20868$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21125689$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kureshy, Rukhsana I.</creatorcontrib><creatorcontrib>Kumar, Manish</creatorcontrib><creatorcontrib>Agrawal, Santosh</creatorcontrib><creatorcontrib>Khan, Noor-Ul H.</creatorcontrib><creatorcontrib>Dangi, Balchand</creatorcontrib><creatorcontrib>Abdi, Sayed H. R.</creatorcontrib><creatorcontrib>Bajaj, Hari C.</creatorcontrib><title>Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>The active catalysts for the enantioselective ring opening (ARO) of meso‐stilbene oxide, cis‐butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(OiPr)4 with poly‐[(R,R)‐N,N′‐bis‐{3‐(1,1‐dimethylethyl)‐5‐methylene salicylidene} cyclohexane‐1,2‐diamine]‐1 and (1R,2R)‐N,N′‐bis[3,5‐di(tert‐butyl)salicylidene] cyclohexane‐1,2‐diamine‐2. These catalysts in the presence of nonracemic imine as an additive provided β‐amino alcohol in excellent yield (99%) and chiral purity (enantiomeric excess (ee) up to 99%) for the ARO of meso‐stilbene oxide with aniline. The same protocol was less effective for the ARO of cyclic epoxides; however, when triphenylphosphine was used as an additive, there was a significant improvement in catalyst performance for the ARO of cyclohexene oxide (yield, 85–90%; ee, 63–67%). Both in situ generated polymeric and monomeric catalysts performed in a similar manner except that the polymeric catalyst Ti(IV)‐1 was more active and recycled several times with retention of enantioselectivity when compared with the monomeric catalyst Ti(IV)‐2, which was nonrecyclable. Chirality, 2011. © 2010 Wiley‐Liss, Inc.</description><subject>Additives</subject><subject>Aniline</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>chiral monomeric and polymeric Ti(IV)</subject><subject>Chirality</subject><subject>Cyclohexene</subject><subject>enantioselective ring opening</subject><subject>meso-epoxides</subject><subject>Oxides</subject><subject>Recycled</subject><subject>salen</subject><subject>syn and anti-β-aminoalcohol</subject><issn>0899-0042</issn><issn>1520-636X</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqNkU1v1DAURS0EokNhww9A3lEqpdix49jLalTaESMQUD521ovzRjU4cYgz7aTix5OStsuK1dPTPfduDiEvOTvijOVv3YXvj3KmlX5EFrzIWaaE-vGYLJg2JmNM5nvkWUo_GWNGCfmU7OWc54XSZkH-nLTQDj4mDOgGf4m0xjQ2DQ69v4YpaGnc0AZTzLCLOz-l9MoPFxRaH3w7fQ4GCOM11rQaaRfD2GDv3ZTXtIltnL9zf7D69oYmCNhSF5su4A7Tc_JkAyHhi9u7T76-OzlfnmXrj6er5fE6c1LkOqudAjRcoDAF18BAb4qqks6ANuBASlHAxgiECmvJjdAKi1y5UpmKSwAn9snrebfr4-8tpsE2PjkMAVqM22Q1L4zKjZITefAgyUspleaGlf-HllIJPqGHM-r6mFKPG9v1voF-tJzZG4X2RqH9p3CCX93ubqsG63v0ztkE8Bm48gHHB6bs8mz1-W40mzs-Dbi770D_y6pSlIX9_uHUrnnxRb8vpP0k_gI1qLfv</recordid><startdate>201101</startdate><enddate>201101</enddate><creator>Kureshy, Rukhsana I.</creator><creator>Kumar, Manish</creator><creator>Agrawal, Santosh</creator><creator>Khan, Noor-Ul H.</creator><creator>Dangi, Balchand</creator><creator>Abdi, Sayed H. R.</creator><creator>Bajaj, Hari C.</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201101</creationdate><title>Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes</title><author>Kureshy, Rukhsana I. ; Kumar, Manish ; Agrawal, Santosh ; Khan, Noor-Ul H. ; Dangi, Balchand ; Abdi, Sayed H. R. ; Bajaj, Hari C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4328-dc6ae913e39518a0a8f5bb4c9a89aca4435af93eabed419386e526c769b14aac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Additives</topic><topic>Aniline</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>chiral monomeric and polymeric Ti(IV)</topic><topic>Chirality</topic><topic>Cyclohexene</topic><topic>enantioselective ring opening</topic><topic>meso-epoxides</topic><topic>Oxides</topic><topic>Recycled</topic><topic>salen</topic><topic>syn and anti-β-aminoalcohol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kureshy, Rukhsana I.</creatorcontrib><creatorcontrib>Kumar, Manish</creatorcontrib><creatorcontrib>Agrawal, Santosh</creatorcontrib><creatorcontrib>Khan, Noor-Ul H.</creatorcontrib><creatorcontrib>Dangi, Balchand</creatorcontrib><creatorcontrib>Abdi, Sayed H. R.</creatorcontrib><creatorcontrib>Bajaj, Hari C.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kureshy, Rukhsana I.</au><au>Kumar, Manish</au><au>Agrawal, Santosh</au><au>Khan, Noor-Ul H.</au><au>Dangi, Balchand</au><au>Abdi, Sayed H. R.</au><au>Bajaj, Hari C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2011-01</date><risdate>2011</risdate><volume>23</volume><issue>1</issue><spage>76</spage><epage>83</epage><pages>76-83</pages><issn>0899-0042</issn><issn>1520-636X</issn><eissn>1520-636X</eissn><abstract>The active catalysts for the enantioselective ring opening (ARO) of meso‐stilbene oxide, cis‐butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(OiPr)4 with poly‐[(R,R)‐N,N′‐bis‐{3‐(1,1‐dimethylethyl)‐5‐methylene salicylidene} cyclohexane‐1,2‐diamine]‐1 and (1R,2R)‐N,N′‐bis[3,5‐di(tert‐butyl)salicylidene] cyclohexane‐1,2‐diamine‐2. These catalysts in the presence of nonracemic imine as an additive provided β‐amino alcohol in excellent yield (99%) and chiral purity (enantiomeric excess (ee) up to 99%) for the ARO of meso‐stilbene oxide with aniline. The same protocol was less effective for the ARO of cyclic epoxides; however, when triphenylphosphine was used as an additive, there was a significant improvement in catalyst performance for the ARO of cyclohexene oxide (yield, 85–90%; ee, 63–67%). Both in situ generated polymeric and monomeric catalysts performed in a similar manner except that the polymeric catalyst Ti(IV)‐1 was more active and recycled several times with retention of enantioselectivity when compared with the monomeric catalyst Ti(IV)‐2, which was nonrecyclable. Chirality, 2011. © 2010 Wiley‐Liss, Inc.</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>21125689</pmid><doi>10.1002/chir.20868</doi><tpages>8</tpages></addata></record> |
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subjects | Additives Aniline Catalysis Catalysts chiral monomeric and polymeric Ti(IV) Chirality Cyclohexene enantioselective ring opening meso-epoxides Oxides Recycled salen syn and anti-β-aminoalcohol |
title | Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes |
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