Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes
During efforts to expand the scope of Lewis‐acid‐catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitros...
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| Veröffentlicht in: | European journal of organic chemistry 2015-08, Vol.2015 (22), p.4900-4906 |
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| container_title | European journal of organic chemistry |
| container_volume | 2015 |
| creator | Vemula, Naresh Pagenkopf, Brian L. |
| description | During efforts to expand the scope of Lewis‐acid‐catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction.
The scope of Yb(OTf)3‐catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid with electron‐rich nitrosoarenes. |
| doi_str_mv | 10.1002/ejoc.201500542 |
| format | Article |
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The scope of Yb(OTf)3‐catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid with electron‐rich nitrosoarenes.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201500542</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Arenes ; Cycloaddition ; Donor-acceptor systems ; Lewis acid catalysis ; Nitrogen heterocycles ; Nitroso compounds ; Small-ring systems</subject><ispartof>European journal of organic chemistry, 2015-08, Vol.2015 (22), p.4900-4906</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4252-389e9ef184888a52d509f0b11741401b525ced95b5e6b57d593f2917c5ccbfe93</citedby><cites>FETCH-LOGICAL-c4252-389e9ef184888a52d509f0b11741401b525ced95b5e6b57d593f2917c5ccbfe93</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.201500542$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201500542$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids></links><search><creatorcontrib>Vemula, Naresh</creatorcontrib><creatorcontrib>Pagenkopf, Brian L.</creatorcontrib><title>Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>During efforts to expand the scope of Lewis‐acid‐catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction.
The scope of Yb(OTf)3‐catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid with electron‐rich nitrosoarenes.</description><subject>Arenes</subject><subject>Cycloaddition</subject><subject>Donor-acceptor systems</subject><subject>Lewis acid catalysis</subject><subject>Nitrogen heterocycles</subject><subject>Nitroso compounds</subject><subject>Small-ring systems</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkEtPwzAQhCMEEs8r50hccVk7cRIfq1AKVdUiKKI3y7Ed4VLiYqdA-PWEBipunHY1mm92NUFwiqGHAciFXljZI4ApAI3JTnCAgTEECYPddo-jGGEWzfeDQ-8XAMCSBB8EzX1T1U_aGx_aMpzp2omnRjmL8DlB9kN8mkr7UFQqvG2cs0ujNsKbEWHeyKUVSpna2GqDX9rKOtSXUq9q6zpDsa7Fb8TE1M56K5xuleNgrxRLr09-5lHwcDWY5ddoPB3e5P0xkjGhBEUZ00yXOIuzLBOUKAqshALjNMYx4IISKrVitKA6KWiqKItKwnAqqZRFqVl0FJx1uStnX9fa13xh165qT3KcsDQlmABpXb3OJdsPvdMlXznzIlzDMfDvevl3vXxbbwuwDng3S9384-aD0TT_y6KONb7WH1tWuGeepFFK-eNkyPNoNJ8P7-_4LPoCKP2Pkw</recordid><startdate>201508</startdate><enddate>201508</enddate><creator>Vemula, Naresh</creator><creator>Pagenkopf, Brian L.</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>201508</creationdate><title>Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes</title><author>Vemula, Naresh ; Pagenkopf, Brian L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4252-389e9ef184888a52d509f0b11741401b525ced95b5e6b57d593f2917c5ccbfe93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Arenes</topic><topic>Cycloaddition</topic><topic>Donor-acceptor systems</topic><topic>Lewis acid catalysis</topic><topic>Nitrogen heterocycles</topic><topic>Nitroso compounds</topic><topic>Small-ring systems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vemula, Naresh</creatorcontrib><creatorcontrib>Pagenkopf, Brian L.</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>Vemula, Naresh</au><au>Pagenkopf, Brian L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-08</date><risdate>2015</risdate><volume>2015</volume><issue>22</issue><spage>4900</spage><epage>4906</epage><pages>4900-4906</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>During efforts to expand the scope of Lewis‐acid‐catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction.
The scope of Yb(OTf)3‐catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol‐% of MgI2 was used as a Lewis acid with electron‐rich nitrosoarenes.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201500542</doi><tpages>7</tpages></addata></record> |
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| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Arenes Cycloaddition Donor-acceptor systems Lewis acid catalysis Nitrogen heterocycles Nitroso compounds Small-ring systems |
| title | Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes |
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