Exo-Selective Reductive Macrocyclization of Ynals
A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo...
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| Veröffentlicht in: | Organic letters 2015-03, Vol.17 (6), p.1493-1496 |
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| container_title | Organic letters |
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| creator | Wang, Hengbin Negretti, Solymar Knauff, Allison R Montgomery, John |
| description | A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity. |
| doi_str_mv | 10.1021/acs.orglett.5b00381 |
| format | Article |
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A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b00381</identifier><identifier>PMID: 25746060</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; carbenes ; Catalysis ; catalysts ; chemical reactions ; chemical structure ; Cyclization ; Macrocyclic Compounds - chemical synthesis ; Macrocyclic Compounds - chemistry ; Methane - analogs & derivatives ; Methane - chemistry ; Molecular Structure ; Nickel - chemistry ; regioselectivity ; Stereoisomerism</subject><ispartof>Organic letters, 2015-03, Vol.17 (6), p.1493-1496</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a478t-a0baa46b3af4339925d1c71f61434aeb1eb0667aa3adfd13271b2653041bfad3</citedby><cites>FETCH-LOGICAL-a478t-a0baa46b3af4339925d1c71f61434aeb1eb0667aa3adfd13271b2653041bfad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b00381$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b00381$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25746060$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hengbin</creatorcontrib><creatorcontrib>Negretti, Solymar</creatorcontrib><creatorcontrib>Knauff, Allison R</creatorcontrib><creatorcontrib>Montgomery, John</creatorcontrib><title>Exo-Selective Reductive Macrocyclization of Ynals</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.</description><subject>Alkynes - chemistry</subject><subject>carbenes</subject><subject>Catalysis</subject><subject>catalysts</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Cyclization</subject><subject>Macrocyclic Compounds - chemical synthesis</subject><subject>Macrocyclic Compounds - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Molecular Structure</subject><subject>Nickel - chemistry</subject><subject>regioselectivity</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUU1LAzEQDaLY-vELBOnRy7aZJJu0F0FK_YCKoL14CrPZbN2y3dTNbrH-elO6Fr3oaYaZ9x4z7xFyAbQPlMEAje-7al7Yuu7HCaV8CAekCzHjkaIxO9z3knbIifcLSiFMRsekw2IlZJh3CUw-XPRiC2vqfG17zzZtdt0jmsqZjSnyT6xzV_Zc1nstsfBn5CgLxZ639ZTMbiez8X00fbp7GN9MIxRqWEdIE0QhE46Z4Hw0YnEKRkEmQXCBNgGbUCkVIsc0S4EzBQmTMacCkgxTfkqud7KrJlna1NiyrrDQqypfYrXRDnP9e1Pmb3ru1loEH5RQQeCqFajce2N9rZe5N7YosLSu8ZpRRoeKcQn_QkHKGFi4WwYo30GDO95XNttfBFRvY9EhFt3GottYAuvy5zN7zncOATDYAbbshWuqrdN_Sn4Bs02cXA</recordid><startdate>20150320</startdate><enddate>20150320</enddate><creator>Wang, Hengbin</creator><creator>Negretti, Solymar</creator><creator>Knauff, Allison R</creator><creator>Montgomery, John</creator><general>American Chemical Society</general><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><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20150320</creationdate><title>Exo-Selective Reductive Macrocyclization of Ynals</title><author>Wang, Hengbin ; Negretti, Solymar ; Knauff, Allison R ; Montgomery, John</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a478t-a0baa46b3af4339925d1c71f61434aeb1eb0667aa3adfd13271b2653041bfad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkynes - chemistry</topic><topic>carbenes</topic><topic>Catalysis</topic><topic>catalysts</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Cyclization</topic><topic>Macrocyclic Compounds - chemical synthesis</topic><topic>Macrocyclic Compounds - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Molecular Structure</topic><topic>Nickel - chemistry</topic><topic>regioselectivity</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hengbin</creatorcontrib><creatorcontrib>Negretti, Solymar</creatorcontrib><creatorcontrib>Knauff, Allison R</creatorcontrib><creatorcontrib>Montgomery, John</creatorcontrib><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><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hengbin</au><au>Negretti, Solymar</au><au>Knauff, Allison R</au><au>Montgomery, John</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exo-Selective Reductive Macrocyclization of Ynals</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-03-20</date><risdate>2015</risdate><volume>17</volume><issue>6</issue><spage>1493</spage><epage>1496</epage><pages>1493-1496</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25746060</pmid><doi>10.1021/acs.orglett.5b00381</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Organic letters, 2015-03, Vol.17 (6), p.1493-1496 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alkynes - chemistry carbenes Catalysis catalysts chemical reactions chemical structure Cyclization Macrocyclic Compounds - chemical synthesis Macrocyclic Compounds - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure Nickel - chemistry regioselectivity Stereoisomerism |
| title | Exo-Selective Reductive Macrocyclization of Ynals |
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