N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones
The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐/δ‐amino‐α,β‐unsaturated ketones were developed, giving the corresponding pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities. Pyrrolidones and p...
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| Veröffentlicht in: | Chemistry : a European journal 2018-06, Vol.24 (33), p.8302-8305 |
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| container_issue | 33 |
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| container_title | Chemistry : a European journal |
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| creator | Zhang, Zhao‐Fei Zhang, Chun‐Lin Song, Zhi‐Yong Gao, Zhong‐Hua Ye, Song |
| description | The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐/δ‐amino‐α,β‐unsaturated ketones were developed, giving the corresponding pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.
Pyrrolidones and piperidones: The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐ or δ‐amino‐α,β‐unsaturated ketones were developed to give 3,4‐disubstituted pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities. |
| doi_str_mv | 10.1002/chem.201801539 |
| format | Article |
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Pyrrolidones and piperidones: The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐ or δ‐amino‐α,β‐unsaturated ketones were developed to give 3,4‐disubstituted pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201801539</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>annulation ; carbene catalysis ; Chemical reactions ; Chemical synthesis ; Chemistry ; Enantiomers ; enantioselectivity ; Ketones ; Organic chemistry ; piperidones ; pyrrolidones</subject><ispartof>Chemistry : a European journal, 2018-06, Vol.24 (33), p.8302-8305</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3509-6a68b8d5f8d8fdf51e7bc313a4d717a5a083605c72739a67bcdc3a47700693213</citedby><cites>FETCH-LOGICAL-c3509-6a68b8d5f8d8fdf51e7bc313a4d717a5a083605c72739a67bcdc3a47700693213</cites><orcidid>0000-0002-3962-7738</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201801539$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201801539$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Zhang, Zhao‐Fei</creatorcontrib><creatorcontrib>Zhang, Chun‐Lin</creatorcontrib><creatorcontrib>Song, Zhi‐Yong</creatorcontrib><creatorcontrib>Gao, Zhong‐Hua</creatorcontrib><creatorcontrib>Ye, Song</creatorcontrib><title>N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones</title><title>Chemistry : a European journal</title><description>The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐/δ‐amino‐α,β‐unsaturated ketones were developed, giving the corresponding pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.
Pyrrolidones and piperidones: The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐ or δ‐amino‐α,β‐unsaturated ketones were developed to give 3,4‐disubstituted pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.</description><subject>annulation</subject><subject>carbene catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Enantiomers</subject><subject>enantioselectivity</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>piperidones</subject><subject>pyrrolidones</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkUFu1DAYhSNEJYbClrUlNizI1I7rxGE3igYGUUol6Dry2H8UVx57sJ1WYcURuEoBiVvkED0JjqYCiQ0bP_l_33u29GfZM4KXBOPiRPawWxaYcEwYrR9kC8IKktOqZA-zBa5Pq7xM80fZ4xCuMMZ1Seki-3V-9_XbBiJ4J0dptESN8FuwkMaNiMKMX0ChlbWDEVE7i1yHptvZ7I3zThgF_aggoBsdezT9SM7J9DOdq522Lul0-3L6nvTSBhEHL2KqewfRWQiv0NoKm1oDGJBRXwP6ONrYQ9Bhfudi9N4ZrWYWCavQhd6DP9yfZEedMAGe3utxdvl6_anZ5Gcf3rxtVme5pAzXeSlKvuWKdVzxTnWMQLWVlFBxqipSCSYwpyVmsioqWosymUoms6owLmtaEHqcvTj07r37PECI7U4HCcYIC24IbYGLouaYY5bQ5_-gV27wNv0uUYwRTginiVoeKOldCB66du_1TvixJbid99jOe2z_7DEF6kPgRhsY_0O3zWb9_m_2NxWNr40</recordid><startdate>20180612</startdate><enddate>20180612</enddate><creator>Zhang, Zhao‐Fei</creator><creator>Zhang, Chun‐Lin</creator><creator>Song, Zhi‐Yong</creator><creator>Gao, Zhong‐Hua</creator><creator>Ye, Song</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3962-7738</orcidid></search><sort><creationdate>20180612</creationdate><title>N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones</title><author>Zhang, Zhao‐Fei ; Zhang, Chun‐Lin ; Song, Zhi‐Yong ; Gao, Zhong‐Hua ; Ye, Song</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3509-6a68b8d5f8d8fdf51e7bc313a4d717a5a083605c72739a67bcdc3a47700693213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>annulation</topic><topic>carbene catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Enantiomers</topic><topic>enantioselectivity</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>piperidones</topic><topic>pyrrolidones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhao‐Fei</creatorcontrib><creatorcontrib>Zhang, Chun‐Lin</creatorcontrib><creatorcontrib>Song, Zhi‐Yong</creatorcontrib><creatorcontrib>Gao, Zhong‐Hua</creatorcontrib><creatorcontrib>Ye, Song</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zhao‐Fei</au><au>Zhang, Chun‐Lin</au><au>Song, Zhi‐Yong</au><au>Gao, Zhong‐Hua</au><au>Ye, Song</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones</atitle><jtitle>Chemistry : a European journal</jtitle><date>2018-06-12</date><risdate>2018</risdate><volume>24</volume><issue>33</issue><spage>8302</spage><epage>8305</epage><pages>8302-8305</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐/δ‐amino‐α,β‐unsaturated ketones were developed, giving the corresponding pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.
Pyrrolidones and piperidones: The N‐heterocyclic carbene‐catalyzed [2+3] and [2+4] annulations of α‐chloroaldehydes with γ‐ or δ‐amino‐α,β‐unsaturated ketones were developed to give 3,4‐disubstituted pyrrolidones and piperidones in good yields with exclusive trans‐selectivities and excellent enantioselectivities.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.201801539</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-3962-7738</orcidid></addata></record> |
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| ispartof | Chemistry : a European journal, 2018-06, Vol.24 (33), p.8302-8305 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | annulation carbene catalysis Chemical reactions Chemical synthesis Chemistry Enantiomers enantioselectivity Ketones Organic chemistry piperidones pyrrolidones |
| title | N‐Heterocyclic Carbene‐Catalyzed Annulation of α‐Chloroaldehydes with γ‐/δ‐Amino‐α,β‐Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones |
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