Photocatalytic reverse polarity Povarov reaction
A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating via a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron def...
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| Veröffentlicht in: | Chemical science (Cambridge) 2018-08, Vol.9 (32), p.6653-6658 |
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| creator | Leitch, Jamie A Fuentes de Arriba, Angel L Tan, Joanne Hoff, Oskar Martínez, Carlos M Dixon, Darren J |
| description | A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating
via
a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the
trans
diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.
A reverse polarity photocatalysed Povarov reaction of imines and electron deficient alkenes is described. |
| doi_str_mv | 10.1039/c8sc01704b |
| format | Article |
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via
a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the
trans
diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.
A reverse polarity photocatalysed Povarov reaction of imines and electron deficient alkenes is described.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c8sc01704b</identifier><identifier>PMID: 30310598</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Amino radical ; Aromatic compounds ; Electron transfer ; Electrons ; Free radicals ; Imines ; Iridium ; Lewis acid ; Organic chemistry ; Polarity ; Stereoselectivity ; Substrates</subject><ispartof>Chemical science (Cambridge), 2018-08, Vol.9 (32), p.6653-6658</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-c02f5d653511b1b6b812a17c205b59ca1c55fb0cd224830a498ae50da1a894c33</citedby><cites>FETCH-LOGICAL-c373t-c02f5d653511b1b6b812a17c205b59ca1c55fb0cd224830a498ae50da1a894c33</cites><orcidid>0000-0001-6997-184X ; 0000-0003-2456-5236</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,864,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30310598$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Leitch, Jamie A</creatorcontrib><creatorcontrib>Fuentes de Arriba, Angel L</creatorcontrib><creatorcontrib>Tan, Joanne</creatorcontrib><creatorcontrib>Hoff, Oskar</creatorcontrib><creatorcontrib>Martínez, Carlos M</creatorcontrib><creatorcontrib>Dixon, Darren J</creatorcontrib><title>Photocatalytic reverse polarity Povarov reaction</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating
via
a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the
trans
diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.
A reverse polarity photocatalysed Povarov reaction of imines and electron deficient alkenes is described.</description><subject>Alkenes</subject><subject>Amino radical</subject><subject>Aromatic compounds</subject><subject>Electron transfer</subject><subject>Electrons</subject><subject>Free radicals</subject><subject>Imines</subject><subject>Iridium</subject><subject>Lewis acid</subject><subject>Organic chemistry</subject><subject>Polarity</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkc1LAzEQxYMottRevCsFLyKsziSb3eSoi19QsKCel2w2i1u2TU2yhf73RlsrOJcZeD8ejzeEnCJcIzB5o4XXgDmk1QEZUkgxyTiTh_ubwoCMvZ9DHMaQ0_yYDBgwBC7FkMDswwarVVDdJrR64szaOG8mK9sp14bNZGbXytl1FJQOrV2ekKNGdd6Md3tE3h_u34qnZPry-FzcThPNchYSDbThdYzCESusskogVZhrCrziUivUnDcV6JrSVDBQqRTKcKgVKiFTzdiIXG59V85-9saHctF6bbpOLY3tfUkRpUQpaBbRi3_o3PZuGdOVFIRgWZpRiNTVltLOeu9MU65cu1BuUyKU31WWhXgtfqq8i_D5zrKvFqbeo7_FReBsCziv9-rfL9gXpqd2Dg</recordid><startdate>20180828</startdate><enddate>20180828</enddate><creator>Leitch, Jamie A</creator><creator>Fuentes de Arriba, Angel L</creator><creator>Tan, Joanne</creator><creator>Hoff, Oskar</creator><creator>Martínez, Carlos M</creator><creator>Dixon, Darren J</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6997-184X</orcidid><orcidid>https://orcid.org/0000-0003-2456-5236</orcidid></search><sort><creationdate>20180828</creationdate><title>Photocatalytic reverse polarity Povarov reaction</title><author>Leitch, Jamie A ; Fuentes de Arriba, Angel L ; Tan, Joanne ; Hoff, Oskar ; Martínez, Carlos M ; Dixon, Darren J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-c02f5d653511b1b6b812a17c205b59ca1c55fb0cd224830a498ae50da1a894c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkenes</topic><topic>Amino radical</topic><topic>Aromatic compounds</topic><topic>Electron transfer</topic><topic>Electrons</topic><topic>Free radicals</topic><topic>Imines</topic><topic>Iridium</topic><topic>Lewis acid</topic><topic>Organic chemistry</topic><topic>Polarity</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leitch, Jamie A</creatorcontrib><creatorcontrib>Fuentes de Arriba, Angel L</creatorcontrib><creatorcontrib>Tan, Joanne</creatorcontrib><creatorcontrib>Hoff, Oskar</creatorcontrib><creatorcontrib>Martínez, Carlos M</creatorcontrib><creatorcontrib>Dixon, Darren J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leitch, Jamie A</au><au>Fuentes de Arriba, Angel L</au><au>Tan, Joanne</au><au>Hoff, Oskar</au><au>Martínez, Carlos M</au><au>Dixon, Darren J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic reverse polarity Povarov reaction</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2018-08-28</date><risdate>2018</risdate><volume>9</volume><issue>32</issue><spage>6653</spage><epage>6658</epage><pages>6653-6658</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating
via
a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the
trans
diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.
A reverse polarity photocatalysed Povarov reaction of imines and electron deficient alkenes is described.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30310598</pmid><doi>10.1039/c8sc01704b</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-6997-184X</orcidid><orcidid>https://orcid.org/0000-0003-2456-5236</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical science (Cambridge), 2018-08, Vol.9 (32), p.6653-6658 |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Alkenes Amino radical Aromatic compounds Electron transfer Electrons Free radicals Imines Iridium Lewis acid Organic chemistry Polarity Stereoselectivity Substrates |
| title | Photocatalytic reverse polarity Povarov reaction |
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