Solid Supported 9-Amino-9-deoxy-epi-quinine as Efficient Organocatalyst for Stereoselective Reactions in Batch and Under Continuous Flow Conditions
Polystyrene‐supported 9‐amino‐9‐deoxy‐epi‐quinine was synthesized through co‐polymerization of an ad hoc‐designed chiral monomer with divinylbenzene, in the presence of azobis(isobutyronitile) (AIBN) as radical initiator and toluene and 1‐dodecanol as porogenic solvents. The heterogenized catalyst e...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2015-02, Vol.357 (2-3), p.377-383 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Porta, Riccardo Benaglia, Maurizio Coccia, Francesca Cozzi, Franco Puglisi, Alessandra |
| description | Polystyrene‐supported 9‐amino‐9‐deoxy‐epi‐quinine was synthesized through co‐polymerization of an ad hoc‐designed chiral monomer with divinylbenzene, in the presence of azobis(isobutyronitile) (AIBN) as radical initiator and toluene and 1‐dodecanol as porogenic solvents. The heterogenized catalyst efficiently promoted the reaction of isobutyric aldehyde with β‐nitrostyrene, in very high yield and enantioselectivity, comparable or even higher than that of the homogeneous counterpart (up to 95% ee). The recyclability of the catalyst, its general applicability and its successful application to other reactions was also demonstrated. Finally, for the first time, a 9‐amino‐epi‐quinine derivative was employed to perform an enantioselective Michael reaction under continuous‐flow conditions; by using a home‐made, packed‐bed catalytic reactor, the aldehyde addition to nitrostyrene was successfully realized in flow mode, leading to the product in up to 93% ee. |
| doi_str_mv | 10.1002/adsc.201400821 |
| format | Article |
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The heterogenized catalyst efficiently promoted the reaction of isobutyric aldehyde with β‐nitrostyrene, in very high yield and enantioselectivity, comparable or even higher than that of the homogeneous counterpart (up to 95% ee). The recyclability of the catalyst, its general applicability and its successful application to other reactions was also demonstrated. Finally, for the first time, a 9‐amino‐epi‐quinine derivative was employed to perform an enantioselective Michael reaction under continuous‐flow conditions; by using a home‐made, packed‐bed catalytic reactor, the aldehyde addition to nitrostyrene was successfully realized in flow mode, leading to the product in up to 93% ee.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201400821</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes ; aminocatalysis ; Catalysis ; Catalysts ; catalytic reactor ; Copolymerization ; Derivatives ; Monomers ; organocatalysis ; Radicals ; stereoselective synthesis ; supported catalysts ; Toluene</subject><ispartof>Advanced synthesis & catalysis, 2015-02, Vol.357 (2-3), p.377-383</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5331-78b89b7aa15a1510f39cd339689ef73d91bb8878ea8808cf7d0581dab66d5a2a3</citedby><cites>FETCH-LOGICAL-c5331-78b89b7aa15a1510f39cd339689ef73d91bb8878ea8808cf7d0581dab66d5a2a3</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%2Fadsc.201400821$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201400821$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids></links><search><creatorcontrib>Porta, Riccardo</creatorcontrib><creatorcontrib>Benaglia, Maurizio</creatorcontrib><creatorcontrib>Coccia, Francesca</creatorcontrib><creatorcontrib>Cozzi, Franco</creatorcontrib><creatorcontrib>Puglisi, Alessandra</creatorcontrib><title>Solid Supported 9-Amino-9-deoxy-epi-quinine as Efficient Organocatalyst for Stereoselective Reactions in Batch and Under Continuous Flow Conditions</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>Polystyrene‐supported 9‐amino‐9‐deoxy‐epi‐quinine was synthesized through co‐polymerization of an ad hoc‐designed chiral monomer with divinylbenzene, in the presence of azobis(isobutyronitile) (AIBN) as radical initiator and toluene and 1‐dodecanol as porogenic solvents. The heterogenized catalyst efficiently promoted the reaction of isobutyric aldehyde with β‐nitrostyrene, in very high yield and enantioselectivity, comparable or even higher than that of the homogeneous counterpart (up to 95% ee). The recyclability of the catalyst, its general applicability and its successful application to other reactions was also demonstrated. Finally, for the first time, a 9‐amino‐epi‐quinine derivative was employed to perform an enantioselective Michael reaction under continuous‐flow conditions; by using a home‐made, packed‐bed catalytic reactor, the aldehyde addition to nitrostyrene was successfully realized in flow mode, leading to the product in up to 93% ee.</description><subject>Aldehydes</subject><subject>aminocatalysis</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>catalytic reactor</subject><subject>Copolymerization</subject><subject>Derivatives</subject><subject>Monomers</subject><subject>organocatalysis</subject><subject>Radicals</subject><subject>stereoselective synthesis</subject><subject>supported catalysts</subject><subject>Toluene</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkE1vEzEQhlcIJErhytlHLk7t9a4_jkloCqhqEaHiaHntWTBs7K3tpc3v4A-zISjihjTSzEjPMxq9VfWakgUlpL4wLttFTWhDiKzpk-qMctrihnL19DS35Hn1IufvhFAhhTirfm3j4B3aTuMYUwGHFF7ufIhYYQfxcY9h9Ph-8sEHQCajy7731kMo6DZ9NSFaU8ywzwX1MaFtgQQxwwC2-J-APoGZhxgy8gGtTLHfkAkO3QUHCa1jKD5MccpoM8SHw-78H_pl9aw3Q4ZXf_t5dbe5_Lx-h69vr96vl9fYtoxRLGQnVSeMoe1clPRMWceY4lJBL5hTtOukFBKMlETaXjjSSupMx7lrTW3YefXmeHdM8X6CXPTOZwvDYALMb2nKuZINb-tmRhdH1KaYc4Jej8nvTNprSvQhfX1IX5_SnwV1FB78APv_0Hr5drv-18VH1-cCjyfXpB-aCyZa_eXmSm_IqvnYfLjRK_YbZwCafA</recordid><startdate>20150209</startdate><enddate>20150209</enddate><creator>Porta, Riccardo</creator><creator>Benaglia, Maurizio</creator><creator>Coccia, Francesca</creator><creator>Cozzi, Franco</creator><creator>Puglisi, Alessandra</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20150209</creationdate><title>Solid Supported 9-Amino-9-deoxy-epi-quinine as Efficient Organocatalyst for Stereoselective Reactions in Batch and Under Continuous Flow Conditions</title><author>Porta, Riccardo ; Benaglia, Maurizio ; Coccia, Francesca ; Cozzi, Franco ; Puglisi, Alessandra</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5331-78b89b7aa15a1510f39cd339689ef73d91bb8878ea8808cf7d0581dab66d5a2a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aldehydes</topic><topic>aminocatalysis</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>catalytic reactor</topic><topic>Copolymerization</topic><topic>Derivatives</topic><topic>Monomers</topic><topic>organocatalysis</topic><topic>Radicals</topic><topic>stereoselective synthesis</topic><topic>supported catalysts</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Porta, Riccardo</creatorcontrib><creatorcontrib>Benaglia, Maurizio</creatorcontrib><creatorcontrib>Coccia, Francesca</creatorcontrib><creatorcontrib>Cozzi, Franco</creatorcontrib><creatorcontrib>Puglisi, Alessandra</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Porta, Riccardo</au><au>Benaglia, Maurizio</au><au>Coccia, Francesca</au><au>Cozzi, Franco</au><au>Puglisi, Alessandra</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid Supported 9-Amino-9-deoxy-epi-quinine as Efficient Organocatalyst for Stereoselective Reactions in Batch and Under Continuous Flow Conditions</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2015-02-09</date><risdate>2015</risdate><volume>357</volume><issue>2-3</issue><spage>377</spage><epage>383</epage><pages>377-383</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Polystyrene‐supported 9‐amino‐9‐deoxy‐epi‐quinine was synthesized through co‐polymerization of an ad hoc‐designed chiral monomer with divinylbenzene, in the presence of azobis(isobutyronitile) (AIBN) as radical initiator and toluene and 1‐dodecanol as porogenic solvents. The heterogenized catalyst efficiently promoted the reaction of isobutyric aldehyde with β‐nitrostyrene, in very high yield and enantioselectivity, comparable or even higher than that of the homogeneous counterpart (up to 95% ee). The recyclability of the catalyst, its general applicability and its successful application to other reactions was also demonstrated. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes aminocatalysis Catalysis Catalysts catalytic reactor Copolymerization Derivatives Monomers organocatalysis Radicals stereoselective synthesis supported catalysts Toluene |
| title | Solid Supported 9-Amino-9-deoxy-epi-quinine as Efficient Organocatalyst for Stereoselective Reactions in Batch and Under Continuous Flow Conditions |
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