A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence
We report herein a method based on a radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) to produce an atom transfer radical addition (ATRA) adduct, which subseqently underwent an acid‐mediated lactonization. Thi...
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| Veröffentlicht in: | European journal of organic chemistry 2016-03, Vol.2016 (9), p.1739-1750 |
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| container_title | European journal of organic chemistry |
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| creator | León-Rayo, David F. Morales-Chamorro, Maricela Cordero-Vargas, Alejandro |
| description | We report herein a method based on a radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) to produce an atom transfer radical addition (ATRA) adduct, which subseqently underwent an acid‐mediated lactonization. This approach can be described as a free radical reaction followed by an intermolecular iodolactonization. Twenty‐two experiments were carried out to evaluate the scope of the reaction, which afforded a wide variety of iodo lactones with diverse functionalities. The utility of this approach was demonstrated in the synthesis of the natural product (–)‐de‐O‐methylcentrolobine.
A radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) produced the adduct of an atom transfer radical addition (ATRA), which underwent an acid‐mediated lactonization to afford the corresponding iodolactone. This approach can be described as a formal intermolecular iodolactonization. |
| doi_str_mv | 10.1002/ejoc.201600051 |
| format | Article |
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A radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) produced the adduct of an atom transfer radical addition (ATRA), which underwent an acid‐mediated lactonization to afford the corresponding iodolactone. This approach can be described as a formal intermolecular iodolactonization.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201600051</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Allylic compounds ; Carboxylic acids ; Lactones ; Radical reactions ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2016-03, Vol.2016 (9), p.1739-1750</ispartof><rights>Copyright © 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4211-7e5bac9af62f6deff505a14c69f906b32a6a305d2d1561c51771d6b424928d23</citedby><cites>FETCH-LOGICAL-c4211-7e5bac9af62f6deff505a14c69f906b32a6a305d2d1561c51771d6b424928d23</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%2Fejoc.201600051$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201600051$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>León-Rayo, David F.</creatorcontrib><creatorcontrib>Morales-Chamorro, Maricela</creatorcontrib><creatorcontrib>Cordero-Vargas, Alejandro</creatorcontrib><title>A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>We report herein a method based on a radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) to produce an atom transfer radical addition (ATRA) adduct, which subseqently underwent an acid‐mediated lactonization. This approach can be described as a free radical reaction followed by an intermolecular iodolactonization. Twenty‐two experiments were carried out to evaluate the scope of the reaction, which afforded a wide variety of iodo lactones with diverse functionalities. The utility of this approach was demonstrated in the synthesis of the natural product (–)‐de‐O‐methylcentrolobine.
A radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) produced the adduct of an atom transfer radical addition (ATRA), which underwent an acid‐mediated lactonization to afford the corresponding iodolactone. This approach can be described as a formal intermolecular iodolactonization.</description><subject>Allylic compounds</subject><subject>Carboxylic acids</subject><subject>Lactones</subject><subject>Radical reactions</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAYhoMoOKdXzwXPnfnd5TjHrJ3DwRwoXkKWpNDZNTPp0PnXm1EZ3jzlDTzP9_G9AFwjOEAQ4lu7dnqAIeIQQoZOQA9BIVLIBTyNmRKaIkFez8FFCOuICM5RDyxHyb3zG1UnRdNav3G11bta-aRwxtVKt66pvlVbuSZZ2Pg9hDsVrEliUMlCmUqrOi0ippNn-7GzjbaX4KxUdbBXv28fLO8ny_FDOpvnxXg0SzXFCKWZZSulhSo5LrmxZckgU4hqLkoB-YpgxRWBzGCDGEeaoSxDhq8opgIPDSZ9cNON3XoXF4dWrt3ON3GjjCjL0JDGi_tg0FHauxC8LeXWVxvl9xJBeShOHoqTx-KiIDrhs6rt_h9aTqbz8V837dwqtPbr6Cr_LnlGMiZfnnKZjx_zGaFT-UZ-AHLCgIA</recordid><startdate>201603</startdate><enddate>201603</enddate><creator>León-Rayo, David F.</creator><creator>Morales-Chamorro, Maricela</creator><creator>Cordero-Vargas, Alejandro</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201603</creationdate><title>A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence</title><author>León-Rayo, David F. ; Morales-Chamorro, Maricela ; Cordero-Vargas, Alejandro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4211-7e5bac9af62f6deff505a14c69f906b32a6a305d2d1561c51771d6b424928d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Allylic compounds</topic><topic>Carboxylic acids</topic><topic>Lactones</topic><topic>Radical reactions</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>León-Rayo, David F.</creatorcontrib><creatorcontrib>Morales-Chamorro, Maricela</creatorcontrib><creatorcontrib>Cordero-Vargas, Alejandro</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>León-Rayo, David F.</au><au>Morales-Chamorro, Maricela</au><au>Cordero-Vargas, Alejandro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2016-03</date><risdate>2016</risdate><volume>2016</volume><issue>9</issue><spage>1739</spage><epage>1750</epage><pages>1739-1750</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We report herein a method based on a radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) to produce an atom transfer radical addition (ATRA) adduct, which subseqently underwent an acid‐mediated lactonization. This approach can be described as a free radical reaction followed by an intermolecular iodolactonization. Twenty‐two experiments were carried out to evaluate the scope of the reaction, which afforded a wide variety of iodo lactones with diverse functionalities. The utility of this approach was demonstrated in the synthesis of the natural product (–)‐de‐O‐methylcentrolobine.
A radical‐ionic sequence between an allylic alcohol and an α‐iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) produced the adduct of an atom transfer radical addition (ATRA), which underwent an acid‐mediated lactonization to afford the corresponding iodolactone. This approach can be described as a formal intermolecular iodolactonization.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201600051</doi><tpages>12</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Allylic compounds Carboxylic acids Lactones Radical reactions Synthetic methods |
| title | A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence |
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