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Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans
A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative c...
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| Published in: | Tetrahedron 2011-03, Vol.67 (10), p.1768-1773 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c426t-d516fa4191324331c2fe76df1dd29ca260e5eaa6dfa0de97665dbc33ede226a73 |
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| cites | cdi_FETCH-LOGICAL-c426t-d516fa4191324331c2fe76df1dd29ca260e5eaa6dfa0de97665dbc33ede226a73 |
| container_end_page | 1773 |
| container_issue | 10 |
| container_start_page | 1768 |
| container_title | Tetrahedron |
| container_volume | 67 |
| creator | Liu, Wen Zhou, Jing Zheng, Changwu Chen, Xingkuan Xiao, Hua Yang, Yingquan Guo, Yinlong Zhao, Gang |
| description | A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20
mol
%) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.01.036 |
| format | article |
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mol
%) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.01.036</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>3,4-Dihydropyrans ; Activated ; Activated alkenes ; Alkenes ; Catalysis ; Catalysts ; Catalysts: preparations and properties ; Chemistry ; Cyclization reaction ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Ketones ; Organic chemistry ; Preparations and properties ; Rauhut–Currier reaction ; Stereoselectivity ; Tetrahedrons ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Tetrahedron, 2011-03, Vol.67 (10), p.1768-1773</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c426t-d516fa4191324331c2fe76df1dd29ca260e5eaa6dfa0de97665dbc33ede226a73</citedby><cites>FETCH-LOGICAL-c426t-d516fa4191324331c2fe76df1dd29ca260e5eaa6dfa0de97665dbc33ede226a73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23900894$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Wen</creatorcontrib><creatorcontrib>Zhou, Jing</creatorcontrib><creatorcontrib>Zheng, Changwu</creatorcontrib><creatorcontrib>Chen, Xingkuan</creatorcontrib><creatorcontrib>Xiao, Hua</creatorcontrib><creatorcontrib>Yang, Yingquan</creatorcontrib><creatorcontrib>Guo, Yinlong</creatorcontrib><creatorcontrib>Zhao, Gang</creatorcontrib><title>Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans</title><title>Tetrahedron</title><description>A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20
mol
%) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.
[Display omitted]</description><subject>3,4-Dihydropyrans</subject><subject>Activated</subject><subject>Activated alkenes</subject><subject>Alkenes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Cyclization reaction</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Rauhut–Currier reaction</subject><subject>Stereoselectivity</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kM1qGzEQx0VpoM7HA_SmS6CHrjP6sJylp2KaDwgEQnoWU2m2lrvedSStYXPqO_QN8ySR7ZBjYZAG8Zu_mB9jnwVMBQhzsZpmylMJQkyhlDIf2ERoo6uZFuYjmwBoqDRI-MSOU1oBFFKqCRsfsfO05i72KVUPOCyH_PL332KIMVC8cKNrwzPm0Hc8Erpdk3jf8F27xUyeY_uHOko89_x32BL31CVqR94M3R7HElAw9VVXPixHH_vNGLFLp-yowTbR2dt9wn5e_Xhc3FR399e3i-93ldPS5MrPhGlQi1ooqZUSTjY0N74R3svaoTRAM0IsLwie6rkxM__LKUWepDQ4VyfsyyF3E_ungVK265ActS121A_JirnW5rKcsqDigO5tRGrsJoY1xtEKsDvNdmWLZrvTbKGUMmXm_C0ek8O2Kau5kN4HpaoBLmtduG8Hjsqu2-LWJheoc-RDJJet78N_fnkFwqyWcQ</recordid><startdate>20110311</startdate><enddate>20110311</enddate><creator>Liu, Wen</creator><creator>Zhou, Jing</creator><creator>Zheng, Changwu</creator><creator>Chen, Xingkuan</creator><creator>Xiao, Hua</creator><creator>Yang, Yingquan</creator><creator>Guo, Yinlong</creator><creator>Zhao, Gang</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110311</creationdate><title>Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans</title><author>Liu, Wen ; Zhou, Jing ; Zheng, Changwu ; Chen, Xingkuan ; Xiao, Hua ; Yang, Yingquan ; Guo, Yinlong ; Zhao, Gang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-d516fa4191324331c2fe76df1dd29ca260e5eaa6dfa0de97665dbc33ede226a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>3,4-Dihydropyrans</topic><topic>Activated</topic><topic>Activated alkenes</topic><topic>Alkenes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Cyclization reaction</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Rauhut–Currier reaction</topic><topic>Stereoselectivity</topic><topic>Tetrahedrons</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Wen</creatorcontrib><creatorcontrib>Zhou, Jing</creatorcontrib><creatorcontrib>Zheng, Changwu</creatorcontrib><creatorcontrib>Chen, Xingkuan</creatorcontrib><creatorcontrib>Xiao, Hua</creatorcontrib><creatorcontrib>Yang, Yingquan</creatorcontrib><creatorcontrib>Guo, Yinlong</creatorcontrib><creatorcontrib>Zhao, Gang</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Wen</au><au>Zhou, Jing</au><au>Zheng, Changwu</au><au>Chen, Xingkuan</au><au>Xiao, Hua</au><au>Yang, Yingquan</au><au>Guo, Yinlong</au><au>Zhao, Gang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans</atitle><jtitle>Tetrahedron</jtitle><date>2011-03-11</date><risdate>2011</risdate><volume>67</volume><issue>10</issue><spage>1768</spage><epage>1773</epage><pages>1768-1773</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A novel tandem cross-Rauhut–Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20
mol
%) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.
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| fulltext | fulltext |
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| ispartof | Tetrahedron, 2011-03, Vol.67 (10), p.1768-1773 |
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| language | eng |
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| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | 3,4-Dihydropyrans Activated Activated alkenes Alkenes Catalysis Catalysts Catalysts: preparations and properties Chemistry Cyclization reaction Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Ketones Organic chemistry Preparations and properties Rauhut–Currier reaction Stereoselectivity Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans |
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