Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes
The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phos...
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| Veröffentlicht in: | Chemistry : a European journal 2015-02, Vol.21 (6), p.2348-2352 |
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| container_title | Chemistry : a European journal |
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| creator | Saha, Satyajit Schneider, Christoph |
| description | The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phosphoric acid catalyst controls the enantioselectivity of the carbon–carbon bond‐forming event. The products are readily converted into other xanthene‐based heterocycles.
With excellent enantio‐ and diastereoselectivity, acetamido‐substituted tetrahydrobenzoxanthenes and related heterocycles are obtained in one synthetic operation. A specifically optimized chiral phosphoric acid converts ortho‐hydroxy benzhydryl alcohols and enamides into highly functionalized target compounds carrying three contiguous chiral centers with typically good overall yields. |
| doi_str_mv | 10.1002/chem.201406044 |
| format | Article |
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With excellent enantio‐ and diastereoselectivity, acetamido‐substituted tetrahydrobenzoxanthenes and related heterocycles are obtained in one synthetic operation. A specifically optimized chiral phosphoric acid converts ortho‐hydroxy benzhydryl alcohols and enamides into highly functionalized target compounds carrying three contiguous chiral centers with typically good overall yields.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201406044</identifier><identifier>PMID: 25488376</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amides - chemistry ; asymmetric catalysis ; Brønsted acids ; Catalysis ; Crystallography, X-Ray ; domino reactions ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Indolequinones - chemistry ; Molecular Conformation ; Naphthols - chemistry ; organocatalysis ; Phosphoric Acids - chemistry ; Stereoisomerism ; xanthenes ; Xanthenes - chemistry</subject><ispartof>Chemistry : a European journal, 2015-02, Vol.21 (6), p.2348-2352</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5564-6b85863e1b44e52bc08949498d4e3b881e9ee11a691539042ba910aa05286c3d3</citedby><cites>FETCH-LOGICAL-c5564-6b85863e1b44e52bc08949498d4e3b881e9ee11a691539042ba910aa05286c3d3</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%2Fchem.201406044$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201406044$$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/25488376$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Saha, Satyajit</creatorcontrib><creatorcontrib>Schneider, Christoph</creatorcontrib><title>Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phosphoric acid catalyst controls the enantioselectivity of the carbon–carbon bond‐forming event. The products are readily converted into other xanthene‐based heterocycles.
With excellent enantio‐ and diastereoselectivity, acetamido‐substituted tetrahydrobenzoxanthenes and related heterocycles are obtained in one synthetic operation. A specifically optimized chiral phosphoric acid converts ortho‐hydroxy benzhydryl alcohols and enamides into highly functionalized target compounds carrying three contiguous chiral centers with typically good overall yields.</description><subject>Amides - chemistry</subject><subject>asymmetric catalysis</subject><subject>Brønsted acids</subject><subject>Catalysis</subject><subject>Crystallography, X-Ray</subject><subject>domino reactions</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Indolequinones - chemistry</subject><subject>Molecular Conformation</subject><subject>Naphthols - chemistry</subject><subject>organocatalysis</subject><subject>Phosphoric Acids - chemistry</subject><subject>Stereoisomerism</subject><subject>xanthenes</subject><subject>Xanthenes - chemistry</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkbGO1DAQhiME4paDlhK5pCCLndhehy6Evd2TbkHoQFdaTjJLDEm82A5sqK6h4HHo6HmTexIc7bGiQy4szXzzaTR_FD0meE4wTp5XDXTzBBOKOab0TjQjLCFxuuDsbjTDGV3EnKXZSfTAuY8Y44yn6f3oJGFUiADNop8v7e9fvfNQo7zSdVwor9rxG9TP0Fp_aNoRLXvVe20ctFB5_QVQXtc6FHpktlOz0zU45A0672-uv19qP8Qr6MGqyWmsb0z8dtC96QFtwDcT_QLl6JXpQhHlu501qmomQWG6XQv7m-sfeQV-EhsP3qpmrK3Zhy2a4HUPo3tb1Tp4dPufRu_Plu-KdXzxZnVe5BdxxRinMS8FEzwFUlIKLCkrLDIanqgppKUQBDIAQhTPSDgQpkmpMoKVwiwRvErr9DR6evCGBT8P4LzstKugbVUPZnCScJbQcHPKAzo_oJU1zlnYyp3VnbKjJFhOMckpJnmMKQw8uXUPZQf1Ef-bSwCyA_BVtzD-RyeL9XLzrzw-zOoQ6_44q-wnyRfpgsmr1yspLsUZTa42skj_AALVszY</recordid><startdate>20150202</startdate><enddate>20150202</enddate><creator>Saha, Satyajit</creator><creator>Schneider, Christoph</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150202</creationdate><title>Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes</title><author>Saha, Satyajit ; Schneider, Christoph</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5564-6b85863e1b44e52bc08949498d4e3b881e9ee11a691539042ba910aa05286c3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amides - chemistry</topic><topic>asymmetric catalysis</topic><topic>Brønsted acids</topic><topic>Catalysis</topic><topic>Crystallography, X-Ray</topic><topic>domino reactions</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Indolequinones - chemistry</topic><topic>Molecular Conformation</topic><topic>Naphthols - chemistry</topic><topic>organocatalysis</topic><topic>Phosphoric Acids - chemistry</topic><topic>Stereoisomerism</topic><topic>xanthenes</topic><topic>Xanthenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Saha, Satyajit</creatorcontrib><creatorcontrib>Schneider, Christoph</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Saha, Satyajit</au><au>Schneider, Christoph</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2015-02-02</date><risdate>2015</risdate><volume>21</volume><issue>6</issue><spage>2348</spage><epage>2352</epage><pages>2348-2352</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The highly enantioselective conjugate addition of enamides and enecarbamates to in situ‐generated ortho‐quinone methides, upon subsequent N,O‐acetalization, gives rise to acetamido‐substituted tetrahydroxanthenes with generally excellent enantio‐ and diastereoselectivities. A chiral BINOL‐based phosphoric acid catalyst controls the enantioselectivity of the carbon–carbon bond‐forming event. The products are readily converted into other xanthene‐based heterocycles.
With excellent enantio‐ and diastereoselectivity, acetamido‐substituted tetrahydrobenzoxanthenes and related heterocycles are obtained in one synthetic operation. A specifically optimized chiral phosphoric acid converts ortho‐hydroxy benzhydryl alcohols and enamides into highly functionalized target compounds carrying three contiguous chiral centers with typically good overall yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25488376</pmid><doi>10.1002/chem.201406044</doi><tpages>5</tpages></addata></record> |
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| subjects | Amides - chemistry asymmetric catalysis Brønsted acids Catalysis Crystallography, X-Ray domino reactions Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Indolequinones - chemistry Molecular Conformation Naphthols - chemistry organocatalysis Phosphoric Acids - chemistry Stereoisomerism xanthenes Xanthenes - chemistry |
| title | Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generated ortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes |
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