Base-Catalyzed Intramolecular 5-exo-dig Cyclization of 2-Propynyl-1,3-dicarbonyl Compounds: An Atom-Economic Route to Stereodefined 2-Methylene-2,3-dihydrofurans
A new and straightforward base‐catalyzed 5‐exo‐trig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds leads to the corresponding stereodefined 2‐methylene‐2,3‐dihydrofurans in excellent yields. A regio‐ and stereoselective 5‐exo‐dig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds under metal‐fre...
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| Veröffentlicht in: | European journal of organic chemistry 2014-08, Vol.2014 (23), p.4999-5003 |
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| container_issue | 23 |
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| container_title | European journal of organic chemistry |
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| creator | Ma, Quan Wang, Yeming Zhao, Yuegang Liao, Peiqiu Sun, Bo Bi, Xihe |
| description | A new and straightforward base‐catalyzed 5‐exo‐trig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds leads to the corresponding stereodefined 2‐methylene‐2,3‐dihydrofurans in excellent yields.
A regio‐ and stereoselective 5‐exo‐dig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds under metal‐free conditions has been developed. This reaction constitutes a new and straightforward method for the efficient synthesis of stereodefined 2‐methylene‐2,3‐dihydrofurans. Spiro‐dihydrofurans can also be prepared in excellent yields by this approach. |
| doi_str_mv | 10.1002/ejoc.201402542 |
| format | Article |
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A regio‐ and stereoselective 5‐exo‐dig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds under metal‐free conditions has been developed. This reaction constitutes a new and straightforward method for the efficient synthesis of stereodefined 2‐methylene‐2,3‐dihydrofurans. Spiro‐dihydrofurans can also be prepared in excellent yields by this approach.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201402542</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkynes ; Base catalysis ; Cyclization ; Intramolecular reactions ; Oxygen heterocycles ; Spiro compounds</subject><ispartof>European journal of organic chemistry, 2014-08, Vol.2014 (23), p.4999-5003</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3552-ffea10d7161f92ca6c0ea95c2262be04cdbfcd00bf4efa83ae541133efa40cbd3</citedby><cites>FETCH-LOGICAL-c3552-ffea10d7161f92ca6c0ea95c2262be04cdbfcd00bf4efa83ae541133efa40cbd3</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.201402542$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201402542$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Ma, Quan</creatorcontrib><creatorcontrib>Wang, Yeming</creatorcontrib><creatorcontrib>Zhao, Yuegang</creatorcontrib><creatorcontrib>Liao, Peiqiu</creatorcontrib><creatorcontrib>Sun, Bo</creatorcontrib><creatorcontrib>Bi, Xihe</creatorcontrib><title>Base-Catalyzed Intramolecular 5-exo-dig Cyclization of 2-Propynyl-1,3-dicarbonyl Compounds: An Atom-Economic Route to Stereodefined 2-Methylene-2,3-dihydrofurans</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A new and straightforward base‐catalyzed 5‐exo‐trig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds leads to the corresponding stereodefined 2‐methylene‐2,3‐dihydrofurans in excellent yields.
A regio‐ and stereoselective 5‐exo‐dig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds under metal‐free conditions has been developed. This reaction constitutes a new and straightforward method for the efficient synthesis of stereodefined 2‐methylene‐2,3‐dihydrofurans. Spiro‐dihydrofurans can also be prepared in excellent yields by this approach.</description><subject>Alkynes</subject><subject>Base catalysis</subject><subject>Cyclization</subject><subject>Intramolecular reactions</subject><subject>Oxygen heterocycles</subject><subject>Spiro compounds</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAUhSMEEqWwZW2JLR78iDM1uyEa-tCUlpfKznKca5oh8R1sRzT9N_2npAyq2LG690jnO2dxiuIlZwvOmHgDW3QLwXjJhCrFo-KAM60pqzR7PP-lLCnX8tvT4llKW8aYrip-UNy9swlobbPtp1toyWnI0Q7Ygxt7G4micIO07b6TenJ9d2tzh4GgJ4JeRtxNYeopfy1nh7OxwVmSGocdjqFNb8kqkFXGga4dBhw6Rz7hmIFkJJ8zRMAWfBfmUkHPIV9PPQSg4k_a9dRG9GO0IT0vnnjbJ3jx9x4WX9-vv9QndHNxfFqvNtRJpQT1Hixn7ZJX3GvhbOUYWK2cEJVogJWubbxrGWt8Cd4eSQuq5FzKWZTMNa08LF7tc3cRf46QstniGMNcafhSqSMplNaza7F3uYgpRfBmF7vBxslwZu5nMPczmIcZZkDvgV9dD9N_3GZ9dlH_y9I926UMNw-sjT9MtZRLZa4-HJuPJ-eXcnMljZa_AXNVngA</recordid><startdate>201408</startdate><enddate>201408</enddate><creator>Ma, Quan</creator><creator>Wang, Yeming</creator><creator>Zhao, Yuegang</creator><creator>Liao, Peiqiu</creator><creator>Sun, Bo</creator><creator>Bi, Xihe</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>201408</creationdate><title>Base-Catalyzed Intramolecular 5-exo-dig Cyclization of 2-Propynyl-1,3-dicarbonyl Compounds: An Atom-Economic Route to Stereodefined 2-Methylene-2,3-dihydrofurans</title><author>Ma, Quan ; Wang, Yeming ; Zhao, Yuegang ; Liao, Peiqiu ; Sun, Bo ; Bi, Xihe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3552-ffea10d7161f92ca6c0ea95c2262be04cdbfcd00bf4efa83ae541133efa40cbd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alkynes</topic><topic>Base catalysis</topic><topic>Cyclization</topic><topic>Intramolecular reactions</topic><topic>Oxygen heterocycles</topic><topic>Spiro compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ma, Quan</creatorcontrib><creatorcontrib>Wang, Yeming</creatorcontrib><creatorcontrib>Zhao, Yuegang</creatorcontrib><creatorcontrib>Liao, Peiqiu</creatorcontrib><creatorcontrib>Sun, Bo</creatorcontrib><creatorcontrib>Bi, Xihe</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>Ma, Quan</au><au>Wang, Yeming</au><au>Zhao, Yuegang</au><au>Liao, Peiqiu</au><au>Sun, Bo</au><au>Bi, Xihe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Base-Catalyzed Intramolecular 5-exo-dig Cyclization of 2-Propynyl-1,3-dicarbonyl Compounds: An Atom-Economic Route to Stereodefined 2-Methylene-2,3-dihydrofurans</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2014-08</date><risdate>2014</risdate><volume>2014</volume><issue>23</issue><spage>4999</spage><epage>5003</epage><pages>4999-5003</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A new and straightforward base‐catalyzed 5‐exo‐trig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds leads to the corresponding stereodefined 2‐methylene‐2,3‐dihydrofurans in excellent yields.
A regio‐ and stereoselective 5‐exo‐dig cyclization of 2‐propynyl‐1,3‐dicarbonyl compounds under metal‐free conditions has been developed. This reaction constitutes a new and straightforward method for the efficient synthesis of stereodefined 2‐methylene‐2,3‐dihydrofurans. Spiro‐dihydrofurans can also be prepared in excellent yields by this approach.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201402542</doi><tpages>5</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes Base catalysis Cyclization Intramolecular reactions Oxygen heterocycles Spiro compounds |
| title | Base-Catalyzed Intramolecular 5-exo-dig Cyclization of 2-Propynyl-1,3-dicarbonyl Compounds: An Atom-Economic Route to Stereodefined 2-Methylene-2,3-dihydrofurans |
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