Kinetic Resolution of 2‐Substituted Indolines by N‐Sulfonylation using an Atropisomeric 4‐DMAP‐N‐oxide Organocatalyst
The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination an...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-05, Vol.56 (21), p.5760-5764 |
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| creator | Murray, James I. Flodén, Nils J. Bauer, Adriano Fessner, Nico D. Dunklemann, Daniel L. Bob‐Egbe, Opetoritse Rzepa, Henry S. Bürgi, Thomas Richardson, Jeffery Spivey, Alan C. |
| description | The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
A practical (re)solution: The kinetic resolution of 2‐substituted indolines by catalytic N‐sulfonylation is reported using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide organocatalyst (see scheme). Vibrational cicrcular dichroism is used to assign the absolute configuration of the catalyst and a qualitative model that accounts for the stereodiscrimination is proposed. |
| doi_str_mv | 10.1002/anie.201700977 |
| format | Article |
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A practical (re)solution: The kinetic resolution of 2‐substituted indolines by catalytic N‐sulfonylation is reported using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide organocatalyst (see scheme). Vibrational cicrcular dichroism is used to assign the absolute configuration of the catalyst and a qualitative model that accounts for the stereodiscrimination is proposed.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201700977</identifier><identifier>PMID: 28444918</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric catalysis ; Catalysis ; Chloride ; Heterocyclic compounds ; indoline ; kinetic resolution ; organocatalysis ; sulfonylation ; Thioglycolic acid</subject><ispartof>Angewandte Chemie International Edition, 2017-05, Vol.56 (21), p.5760-5764</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5167-2bda082fec420f455ed0d5f82e0f99c282b3549081e4a64d2507ba813509a99b3</citedby><cites>FETCH-LOGICAL-c5167-2bda082fec420f455ed0d5f82e0f99c282b3549081e4a64d2507ba813509a99b3</cites><orcidid>0000-0001-6447-7041 ; 0000-0002-8635-8390 ; 0000-0001-5114-490X ; 0000-0001-6179-4519 ; 0000-0002-8668-9261 ; 0000-0002-3376-343X ; 0000-0001-8247-1356 ; 0000-0002-4847-549X ; 0000-0003-0906-082X ; 0000-0002-4450-3828</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%2Fanie.201700977$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201700977$$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/28444918$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Murray, James I.</creatorcontrib><creatorcontrib>Flodén, Nils J.</creatorcontrib><creatorcontrib>Bauer, Adriano</creatorcontrib><creatorcontrib>Fessner, Nico D.</creatorcontrib><creatorcontrib>Dunklemann, Daniel L.</creatorcontrib><creatorcontrib>Bob‐Egbe, Opetoritse</creatorcontrib><creatorcontrib>Rzepa, Henry S.</creatorcontrib><creatorcontrib>Bürgi, Thomas</creatorcontrib><creatorcontrib>Richardson, Jeffery</creatorcontrib><creatorcontrib>Spivey, Alan C.</creatorcontrib><title>Kinetic Resolution of 2‐Substituted Indolines by N‐Sulfonylation using an Atropisomeric 4‐DMAP‐N‐oxide Organocatalyst</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
A practical (re)solution: The kinetic resolution of 2‐substituted indolines by catalytic N‐sulfonylation is reported using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide organocatalyst (see scheme). Vibrational cicrcular dichroism is used to assign the absolute configuration of the catalyst and a qualitative model that accounts for the stereodiscrimination is proposed.</description><subject>asymmetric catalysis</subject><subject>Catalysis</subject><subject>Chloride</subject><subject>Heterocyclic compounds</subject><subject>indoline</subject><subject>kinetic resolution</subject><subject>organocatalysis</subject><subject>sulfonylation</subject><subject>Thioglycolic acid</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqF0ctu1DAUBmALgWgpbFkiS2zYZHp8S-zlqC1l1NIiLuvISZzKlccebEeQVXkEnrFPUk-nFIkNq3Mkf-eXpR-h1wQWBIAeam_NggJpAFTTPEH7RFBSsaZhT8vOGasaKcgeepHSdfFSQv0c7VHJOVdE7qObM-tNtj3-bFJwU7bB4zBievvr95epS9nmKZsBr_wQXJEJdzO-uH90Y_Cz0_cXU7L-CmuPlzmGjU1hbWLJ5AUef1x-KmN7E37aweDLeKV96HXWbk75JXo2apfMq4d5gL69P_l69KE6vzxdHS3Pq16QuqloN2iQdDQ9pzByIcwAgxglNTAq1VNJOya4AkkM1zUfqICm05IwAUor1bED9G6Xu4nh-2RSbtc29cY57U2YUkukooxxKkWhb_-h12GKvvxuq2qgdQ28qMVO9TGkFM3YbqJd6zi3BNptNe22mvaxmnLw5iF26tZmeOR_uihA7cAP68z8n7h2ebE6-Rt-Byewn_U</recordid><startdate>20170515</startdate><enddate>20170515</enddate><creator>Murray, James I.</creator><creator>Flodén, Nils J.</creator><creator>Bauer, Adriano</creator><creator>Fessner, Nico D.</creator><creator>Dunklemann, Daniel L.</creator><creator>Bob‐Egbe, Opetoritse</creator><creator>Rzepa, Henry S.</creator><creator>Bürgi, Thomas</creator><creator>Richardson, Jeffery</creator><creator>Spivey, Alan C.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6447-7041</orcidid><orcidid>https://orcid.org/0000-0002-8635-8390</orcidid><orcidid>https://orcid.org/0000-0001-5114-490X</orcidid><orcidid>https://orcid.org/0000-0001-6179-4519</orcidid><orcidid>https://orcid.org/0000-0002-8668-9261</orcidid><orcidid>https://orcid.org/0000-0002-3376-343X</orcidid><orcidid>https://orcid.org/0000-0001-8247-1356</orcidid><orcidid>https://orcid.org/0000-0002-4847-549X</orcidid><orcidid>https://orcid.org/0000-0003-0906-082X</orcidid><orcidid>https://orcid.org/0000-0002-4450-3828</orcidid></search><sort><creationdate>20170515</creationdate><title>Kinetic Resolution of 2‐Substituted Indolines by N‐Sulfonylation using an Atropisomeric 4‐DMAP‐N‐oxide Organocatalyst</title><author>Murray, James I. ; Flodén, Nils J. ; Bauer, Adriano ; Fessner, Nico D. ; Dunklemann, Daniel L. ; Bob‐Egbe, Opetoritse ; Rzepa, Henry S. ; Bürgi, Thomas ; Richardson, Jeffery ; Spivey, Alan C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5167-2bda082fec420f455ed0d5f82e0f99c282b3549081e4a64d2507ba813509a99b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>asymmetric catalysis</topic><topic>Catalysis</topic><topic>Chloride</topic><topic>Heterocyclic compounds</topic><topic>indoline</topic><topic>kinetic resolution</topic><topic>organocatalysis</topic><topic>sulfonylation</topic><topic>Thioglycolic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Murray, James I.</creatorcontrib><creatorcontrib>Flodén, Nils J.</creatorcontrib><creatorcontrib>Bauer, Adriano</creatorcontrib><creatorcontrib>Fessner, Nico D.</creatorcontrib><creatorcontrib>Dunklemann, Daniel L.</creatorcontrib><creatorcontrib>Bob‐Egbe, Opetoritse</creatorcontrib><creatorcontrib>Rzepa, Henry S.</creatorcontrib><creatorcontrib>Bürgi, Thomas</creatorcontrib><creatorcontrib>Richardson, Jeffery</creatorcontrib><creatorcontrib>Spivey, Alan C.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Murray, James I.</au><au>Flodén, Nils J.</au><au>Bauer, Adriano</au><au>Fessner, Nico D.</au><au>Dunklemann, Daniel L.</au><au>Bob‐Egbe, Opetoritse</au><au>Rzepa, Henry S.</au><au>Bürgi, Thomas</au><au>Richardson, Jeffery</au><au>Spivey, Alan C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kinetic Resolution of 2‐Substituted Indolines by N‐Sulfonylation using an Atropisomeric 4‐DMAP‐N‐oxide Organocatalyst</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-05-15</date><risdate>2017</risdate><volume>56</volume><issue>21</issue><spage>5760</spage><epage>5764</epage><pages>5760-5764</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
A practical (re)solution: The kinetic resolution of 2‐substituted indolines by catalytic N‐sulfonylation is reported using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide organocatalyst (see scheme). Vibrational cicrcular dichroism is used to assign the absolute configuration of the catalyst and a qualitative model that accounts for the stereodiscrimination is proposed.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28444918</pmid><doi>10.1002/anie.201700977</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-6447-7041</orcidid><orcidid>https://orcid.org/0000-0002-8635-8390</orcidid><orcidid>https://orcid.org/0000-0001-5114-490X</orcidid><orcidid>https://orcid.org/0000-0001-6179-4519</orcidid><orcidid>https://orcid.org/0000-0002-8668-9261</orcidid><orcidid>https://orcid.org/0000-0002-3376-343X</orcidid><orcidid>https://orcid.org/0000-0001-8247-1356</orcidid><orcidid>https://orcid.org/0000-0002-4847-549X</orcidid><orcidid>https://orcid.org/0000-0003-0906-082X</orcidid><orcidid>https://orcid.org/0000-0002-4450-3828</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | asymmetric catalysis Catalysis Chloride Heterocyclic compounds indoline kinetic resolution organocatalysis sulfonylation Thioglycolic acid |
| title | Kinetic Resolution of 2‐Substituted Indolines by N‐Sulfonylation using an Atropisomeric 4‐DMAP‐N‐oxide Organocatalyst |
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