Phosphine-Thiourea-Organocatalyzed Asymmetric C−N and C−S Bond Formation Reactions
Phosphine–thiourea based‐organocatalysts derived from l‐proline promoted C−N or C−S bond formation of tert‐butoxycarbonyloxy‐Morita—Baylis—Hillman adducts with phthalimide or alkyl thiols, respectively. Good yields and enantioselectivities up to 93 % were achieved. Phosphine–thiourea‐based organocat...
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| Veröffentlicht in: | Asian journal of organic chemistry 2016-07, Vol.5 (7), p.895-899 |
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| container_title | Asian journal of organic chemistry |
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| creator | Ngo, Thi-Thuy-Duong Nguyen, Thi-Huong Bournaud, Chloée Guillot, Régis Toffano, Martial Vo-Thanh, Giang |
| description | Phosphine–thiourea based‐organocatalysts derived from l‐proline promoted C−N or C−S bond formation of tert‐butoxycarbonyloxy‐Morita—Baylis—Hillman adducts with phthalimide or alkyl thiols, respectively. Good yields and enantioselectivities up to 93 % were achieved.
Phosphine–thiourea‐based organocatalysts derived from l‐proline efficiently promote C−N and C−S bond formation through the asymmetric allylic substitution of tert‐butoxycarbonyloxy‐Morita–Baylis–Hillman (MBH) adducts with phthalimide or alkyl thiols, respectively. The desired products are afforded in good yields and enantioselectivities. |
| doi_str_mv | 10.1002/ajoc.201600212 |
| format | Article |
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Phosphine–thiourea‐based organocatalysts derived from l‐proline efficiently promote C−N and C−S bond formation through the asymmetric allylic substitution of tert‐butoxycarbonyloxy‐Morita–Baylis–Hillman (MBH) adducts with phthalimide or alkyl thiols, respectively. The desired products are afforded in good yields and enantioselectivities.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201600212</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>allylic substitution ; asymmetric synthesis ; l-proline ; Organic chemistry ; organocatalysis ; phthalimide</subject><ispartof>Asian journal of organic chemistry, 2016-07, Vol.5 (7), p.895-899</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3552-97c4ee2d54766622f8968635874450334249068b92ce35d291a4dc4217e3fa73</citedby><cites>FETCH-LOGICAL-c3552-97c4ee2d54766622f8968635874450334249068b92ce35d291a4dc4217e3fa73</cites><orcidid>0000-0003-2682-6698</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.201600212$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201600212$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Ngo, Thi-Thuy-Duong</creatorcontrib><creatorcontrib>Nguyen, Thi-Huong</creatorcontrib><creatorcontrib>Bournaud, Chloée</creatorcontrib><creatorcontrib>Guillot, Régis</creatorcontrib><creatorcontrib>Toffano, Martial</creatorcontrib><creatorcontrib>Vo-Thanh, Giang</creatorcontrib><title>Phosphine-Thiourea-Organocatalyzed Asymmetric C−N and C−S Bond Formation Reactions</title><title>Asian journal of organic chemistry</title><addtitle>Asian J. Org. Chem</addtitle><description>Phosphine–thiourea based‐organocatalysts derived from l‐proline promoted C−N or C−S bond formation of tert‐butoxycarbonyloxy‐Morita—Baylis—Hillman adducts with phthalimide or alkyl thiols, respectively. Good yields and enantioselectivities up to 93 % were achieved.
Phosphine–thiourea‐based organocatalysts derived from l‐proline efficiently promote C−N and C−S bond formation through the asymmetric allylic substitution of tert‐butoxycarbonyloxy‐Morita–Baylis–Hillman (MBH) adducts with phthalimide or alkyl thiols, respectively. The desired products are afforded in good yields and enantioselectivities.</description><subject>allylic substitution</subject><subject>asymmetric synthesis</subject><subject>l-proline</subject><subject>Organic chemistry</subject><subject>organocatalysis</subject><subject>phthalimide</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkM9OwkAQxhujiQS5em7iubj_t3vERlBDQIWot8263UqRdnG3ROsTePYRfRKLNcSbc5lvku83k_mC4BiCPgQAnaql1X0EIGsGiPaCDoICRzSGdH-nAT8Met4vQVOcC4hEJ7i7Xli_XuSlieaL3G6cUdHUPanSalWpVf1u0nDg66Iwlct1mHx9fE5CVaY_ahae2UYOrStUldsyvDVKb4U_Cg4ytfKm99u7wXx4Pk8uovF0dJkMxpHGlKJIcE2MQSklnDGGUBYLFjNMY04IBRgTRARg8aNA2mCaIgEVSTVBkBucKY67wUm7du3sy8b4Si6bF8rmooQxIADGAsWNq9-6tLPeO5PJtcsL5WoJgdymJ7fpyV16DSBa4DVfmfoftxxcTZO_bNSyua_M245V7lkyjjmV95ORFDcPgOEZkxB_A7Y5ggI</recordid><startdate>201607</startdate><enddate>201607</enddate><creator>Ngo, Thi-Thuy-Duong</creator><creator>Nguyen, Thi-Huong</creator><creator>Bournaud, Chloée</creator><creator>Guillot, Régis</creator><creator>Toffano, Martial</creator><creator>Vo-Thanh, Giang</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2682-6698</orcidid></search><sort><creationdate>201607</creationdate><title>Phosphine-Thiourea-Organocatalyzed Asymmetric C−N and C−S Bond Formation Reactions</title><author>Ngo, Thi-Thuy-Duong ; Nguyen, Thi-Huong ; Bournaud, Chloée ; Guillot, Régis ; Toffano, Martial ; Vo-Thanh, Giang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3552-97c4ee2d54766622f8968635874450334249068b92ce35d291a4dc4217e3fa73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>allylic substitution</topic><topic>asymmetric synthesis</topic><topic>l-proline</topic><topic>Organic chemistry</topic><topic>organocatalysis</topic><topic>phthalimide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ngo, Thi-Thuy-Duong</creatorcontrib><creatorcontrib>Nguyen, Thi-Huong</creatorcontrib><creatorcontrib>Bournaud, Chloée</creatorcontrib><creatorcontrib>Guillot, Régis</creatorcontrib><creatorcontrib>Toffano, Martial</creatorcontrib><creatorcontrib>Vo-Thanh, Giang</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ngo, Thi-Thuy-Duong</au><au>Nguyen, Thi-Huong</au><au>Bournaud, Chloée</au><au>Guillot, Régis</au><au>Toffano, Martial</au><au>Vo-Thanh, Giang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphine-Thiourea-Organocatalyzed Asymmetric C−N and C−S Bond Formation Reactions</atitle><jtitle>Asian journal of organic chemistry</jtitle><addtitle>Asian J. Org. Chem</addtitle><date>2016-07</date><risdate>2016</risdate><volume>5</volume><issue>7</issue><spage>895</spage><epage>899</epage><pages>895-899</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>Phosphine–thiourea based‐organocatalysts derived from l‐proline promoted C−N or C−S bond formation of tert‐butoxycarbonyloxy‐Morita—Baylis—Hillman adducts with phthalimide or alkyl thiols, respectively. Good yields and enantioselectivities up to 93 % were achieved.
Phosphine–thiourea‐based organocatalysts derived from l‐proline efficiently promote C−N and C−S bond formation through the asymmetric allylic substitution of tert‐butoxycarbonyloxy‐Morita–Baylis–Hillman (MBH) adducts with phthalimide or alkyl thiols, respectively. The desired products are afforded in good yields and enantioselectivities.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ajoc.201600212</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-2682-6698</orcidid></addata></record> |
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| subjects | allylic substitution asymmetric synthesis l-proline Organic chemistry organocatalysis phthalimide |
| title | Phosphine-Thiourea-Organocatalyzed Asymmetric C−N and C−S Bond Formation Reactions |
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