Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction
Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion reaction, but is diverted by an intramolecular aldol...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-07, Vol.54 (29), p.8485-8489 |
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| container_issue | 29 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Nicolle, Simon M. Lewis, William Hayes, Christopher J. Moody, Christopher J. |
| description | Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion reaction, but is diverted by an intramolecular aldol reaction.
Gone astray: Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. The single‐step reaction proceeds under mild conditions, starting as a carbene OH insertion reaction, but then diverting to an intramolecular aldol reaction. |
| doi_str_mv | 10.1002/anie.201502484 |
| format | Article |
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Gone astray: Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. The single‐step reaction proceeds under mild conditions, starting as a carbene OH insertion reaction, but then diverting to an intramolecular aldol reaction.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201502484</identifier><identifier>PMID: 26068952</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes ; aldol reaction ; Carbenes ; Catalysis ; Copper - chemistry ; diazo compounds ; Furans - chemical synthesis ; Furans - chemistry ; Insertion ; Methane - analogs & derivatives ; Methane - chemical synthesis ; Methane - chemistry ; Rhodium - chemistry ; Stereoisomerism ; Synthesis ; Tetrahydrofuran ; tetrahydrofurans ; transition-metal catalysis</subject><ispartof>Angewandte Chemie International Edition, 2015-07, Vol.54 (29), p.8485-8489</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><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6294-1722f70339b7b61e48f7e2c75977dcabfae0f23885a27e49f07872e951993c0b3</citedby><cites>FETCH-LOGICAL-c6294-1722f70339b7b61e48f7e2c75977dcabfae0f23885a27e49f07872e951993c0b3</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%2Fanie.201502484$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201502484$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26068952$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nicolle, Simon M.</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><creatorcontrib>Hayes, Christopher J.</creatorcontrib><creatorcontrib>Moody, Christopher J.</creatorcontrib><title>Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion reaction, but is diverted by an intramolecular aldol reaction.
Gone astray: Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. The single‐step reaction proceeds under mild conditions, starting as a carbene OH insertion reaction, but then diverting to an intramolecular aldol reaction.</description><subject>Aldehydes</subject><subject>aldol reaction</subject><subject>Carbenes</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>diazo compounds</subject><subject>Furans - chemical synthesis</subject><subject>Furans - chemistry</subject><subject>Insertion</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemical synthesis</subject><subject>Methane - chemistry</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>Tetrahydrofuran</subject><subject>tetrahydrofurans</subject><subject>transition-metal catalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtu1EAURUsIREJgyhDVkImb-n-GkQnpFiGR6PCZlcru57jAbYeqMuD1sBCWxBZwq0OLWUbv6uncM7kIPadkQQlhr3wfYMEIlYQJIx6gYyoZLbjW_OGcBeeFNpIeoScpfZl5Y4h6jI6YIspYyY5RXGeIMCTooM7hO-D11OcWUkh4aPAy3LTdhNdjlXLIY4YNvoYcfTtt4tCM0fcJ5zYO402LX8_tuCNKHyvoAV_9-fV7iVd9mt9h6PF78PUuPEWPGt8leHZ3T9CHN2fX5bK4uDpflacXRa2YFQXVjDWacG4rXSkKwjQaWK2l1XpT-6rxQBrGjZGeaRC2IdpoBlZSa3lNKn6CXu69t3H4NkLKbhtSDV3nexjG5KgWQmlLmL4fVVYZo4gUM7rYo3UcUorQuNsYtj5OjhK3m8TtJnGHSebCizv3WG1hc8D_bTADdg_8CB1M9-jc6eXq7H95se-GlOHnoevjV6c019J9ujx3b_m7jyUpPzvF_wIUUqms</recordid><startdate>20150713</startdate><enddate>20150713</enddate><creator>Nicolle, Simon M.</creator><creator>Lewis, William</creator><creator>Hayes, Christopher J.</creator><creator>Moody, Christopher J.</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><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150713</creationdate><title>Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction</title><author>Nicolle, Simon M. ; Lewis, William ; Hayes, Christopher J. ; Moody, Christopher J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6294-1722f70339b7b61e48f7e2c75977dcabfae0f23885a27e49f07872e951993c0b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aldehydes</topic><topic>aldol reaction</topic><topic>Carbenes</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>diazo compounds</topic><topic>Furans - chemical synthesis</topic><topic>Furans - chemistry</topic><topic>Insertion</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemical synthesis</topic><topic>Methane - chemistry</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><topic>Synthesis</topic><topic>Tetrahydrofuran</topic><topic>tetrahydrofurans</topic><topic>transition-metal catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nicolle, Simon M.</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><creatorcontrib>Hayes, Christopher J.</creatorcontrib><creatorcontrib>Moody, Christopher J.</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><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nicolle, Simon M.</au><au>Lewis, William</au><au>Hayes, Christopher J.</au><au>Moody, Christopher J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-07-13</date><risdate>2015</risdate><volume>54</volume><issue>29</issue><spage>8485</spage><epage>8489</epage><pages>8485-8489</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion reaction, but is diverted by an intramolecular aldol reaction.
Gone astray: Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. The single‐step reaction proceeds under mild conditions, starting as a carbene OH insertion reaction, but then diverting to an intramolecular aldol reaction.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26068952</pmid><doi>10.1002/anie.201502484</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Angewandte Chemie International Edition, 2015-07, Vol.54 (29), p.8485-8489 |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes aldol reaction Carbenes Catalysis Copper - chemistry diazo compounds Furans - chemical synthesis Furans - chemistry Insertion Methane - analogs & derivatives Methane - chemical synthesis Methane - chemistry Rhodium - chemistry Stereoisomerism Synthesis Tetrahydrofuran tetrahydrofurans transition-metal catalysis |
| title | Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction |
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