Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines
The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of re...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-06, Vol.53 (23), p.5964-5968 |
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| creator | Chakrabarty, Shyamal Chatterjee, Indranil Wibbeling, Birgit Daniliuc, Constantin Gabriel Studer, Armido |
| description | The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into α‐amino lactones by reductive or decarboxylative NO cleavage and subsequent lactonisation, and the N‐aryl bond cleavage is also possible under oxidative conditions.
Stereospecific and regioselective: The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor‐activated cyclopropanes with nitrosoarenes offers a novel approach to structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. |
| doi_str_mv | 10.1002/anie.201400885 |
| format | Article |
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Stereospecific and regioselective: The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor‐activated cyclopropanes with nitrosoarenes offers a novel approach to structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201400885</identifier><identifier>PMID: 24764048</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activated ; Bonding ; Borides ; Cleavage ; Cycloaddition ; cycloadditions ; cyclopropanes ; heterocycles ; Isoxazolidines ; Lactones ; Magnesium compounds ; nitrosoarene ; Organic compounds ; stereoselective synthesis</subject><ispartof>Angewandte Chemie International Edition, 2014-06, Vol.53 (23), p.5964-5968</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5215-f3603bbfa76dbe758a978457b481c7f21eff4da326b2ed2183b9d8c97a4725053</citedby><cites>FETCH-LOGICAL-c5215-f3603bbfa76dbe758a978457b481c7f21eff4da326b2ed2183b9d8c97a4725053</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.201400885$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201400885$$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/24764048$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chakrabarty, Shyamal</creatorcontrib><creatorcontrib>Chatterjee, Indranil</creatorcontrib><creatorcontrib>Wibbeling, Birgit</creatorcontrib><creatorcontrib>Daniliuc, Constantin Gabriel</creatorcontrib><creatorcontrib>Studer, Armido</creatorcontrib><title>Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into α‐amino lactones by reductive or decarboxylative NO cleavage and subsequent lactonisation, and the N‐aryl bond cleavage is also possible under oxidative conditions.
Stereospecific and regioselective: The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor‐activated cyclopropanes with nitrosoarenes offers a novel approach to structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity.</description><subject>Activated</subject><subject>Bonding</subject><subject>Borides</subject><subject>Cleavage</subject><subject>Cycloaddition</subject><subject>cycloadditions</subject><subject>cyclopropanes</subject><subject>heterocycles</subject><subject>Isoxazolidines</subject><subject>Lactones</subject><subject>Magnesium compounds</subject><subject>nitrosoarene</subject><subject>Organic compounds</subject><subject>stereoselective synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkUtr3DAUhUVoyKvddlkE3RSCJ3pacnfD5DUkTKAPuihFyLJElHosV_KQTH59NDgdQjZZSVx99-jecwD4iNEEI0ROdOfthCDMEJKS74ADzAkuqBD0Xb4zSgshOd4HhyndZV5KVO6BfcJEyRCTB2D4PthoQ-qt8c4beB7iUrfwNz0mf-Cp70OrI5ytTRt00_jBhw4GNxb6GHrd2QTv_XALF36IIQUdbS59hdMOTvtMaHMLhwDnKTzox9D6xufn92DX6TbZD8_nEfh5fvZjdllc31zMZ9PrwuQleOFoiWhdOy3KpraCS10JybiomcRGOIKtc6zRlJQ1sQ3BktZVI00lNBOEI06PwJdRNw_yb2XToJY-Gdu2eeywSgoLhLN1Jcdvo5xm0_L_JKOfX6F3YRW7vMiGQqSspKCZmoyUybakaJ3qo1_quFYYqU10ahOd2kaXGz49y67qpW22-P-sMlCNwL1v7foNOTVdzM9eihdjr0-Dfdj26vhXlYIKrn4tLhQXV6ii3xaK0CddZLP1</recordid><startdate>20140602</startdate><enddate>20140602</enddate><creator>Chakrabarty, Shyamal</creator><creator>Chatterjee, Indranil</creator><creator>Wibbeling, Birgit</creator><creator>Daniliuc, Constantin Gabriel</creator><creator>Studer, Armido</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7QF</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140602</creationdate><title>Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines</title><author>Chakrabarty, Shyamal ; Chatterjee, Indranil ; Wibbeling, Birgit ; Daniliuc, Constantin Gabriel ; Studer, Armido</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5215-f3603bbfa76dbe758a978457b481c7f21eff4da326b2ed2183b9d8c97a4725053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Activated</topic><topic>Bonding</topic><topic>Borides</topic><topic>Cleavage</topic><topic>Cycloaddition</topic><topic>cycloadditions</topic><topic>cyclopropanes</topic><topic>heterocycles</topic><topic>Isoxazolidines</topic><topic>Lactones</topic><topic>Magnesium compounds</topic><topic>nitrosoarene</topic><topic>Organic compounds</topic><topic>stereoselective synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chakrabarty, Shyamal</creatorcontrib><creatorcontrib>Chatterjee, Indranil</creatorcontrib><creatorcontrib>Wibbeling, Birgit</creatorcontrib><creatorcontrib>Daniliuc, Constantin Gabriel</creatorcontrib><creatorcontrib>Studer, Armido</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Aluminium Industry Abstracts</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>Chakrabarty, Shyamal</au><au>Chatterjee, Indranil</au><au>Wibbeling, Birgit</au><au>Daniliuc, Constantin Gabriel</au><au>Studer, Armido</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. 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Stereospecific and regioselective: The MgBr2‐catalyzed formal [3+2] cycloaddition of donor–acceptor‐activated cyclopropanes with nitrosoarenes offers a novel approach to structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24764048</pmid><doi>10.1002/anie.201400885</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | Activated Bonding Borides Cleavage Cycloaddition cycloadditions cyclopropanes heterocycles Isoxazolidines Lactones Magnesium compounds nitrosoarene Organic compounds stereoselective synthesis |
| title | Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines |
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