Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters
The direct regio- and enantioselective amination of acyclic branched α-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates α-hydrazido-α-alkynyl ketone products with high enantioselectivity. Control experiments indicate that the α-alkyn...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-10, Vol.8 (19), p.5377-5382 |
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| container_title | Organic Chemistry Frontiers |
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| creator | He, Faqian Wang, Jiawen Zhou, Fang Tao, Houchao Yang, Xiaoyu |
| description | The direct regio- and enantioselective amination of acyclic branched α-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates α-hydrazido-α-alkynyl ketone products with high enantioselectivity. Control experiments indicate that the α-alkynyl group in the ketone substrate is critical for both the reactivity and stereoselectivity of the reaction. Facile derivatizations of the functional group-abundant chiral product further highlight the value of this approach in the asymmetric synthesis of α-tertiary amines and N-containing heterocycles. |
| doi_str_mv | 10.1039/D1QO00720C |
| format | Article |
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Control experiments indicate that the α-alkynyl group in the ketone substrate is critical for both the reactivity and stereoselectivity of the reaction. Facile derivatizations of the functional group-abundant chiral product further highlight the value of this approach in the asymmetric synthesis of α-tertiary amines and N-containing heterocycles.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO00720C</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Amination ; Amines ; Asymmetric synthesis ; Asymmetry ; Catalysis ; Enantiomers ; Functional groups ; Ketones ; Organic chemistry ; Phosphoric acid ; Stereoselectivity ; Substrates</subject><ispartof>Organic Chemistry Frontiers, 2021-10, Vol.8 (19), p.5377-5382</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-691be8d91c0c03649702dd2547daacb424f7616ca4bc8736f3e5d32e6a424db73</citedby><cites>FETCH-LOGICAL-c281t-691be8d91c0c03649702dd2547daacb424f7616ca4bc8736f3e5d32e6a424db73</cites><orcidid>0000-0002-0756-0671 ; 0000-0001-7598-0275</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>He, Faqian</creatorcontrib><creatorcontrib>Wang, Jiawen</creatorcontrib><creatorcontrib>Zhou, Fang</creatorcontrib><creatorcontrib>Tao, Houchao</creatorcontrib><creatorcontrib>Yang, Xiaoyu</creatorcontrib><title>Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters</title><title>Organic Chemistry Frontiers</title><description>The direct regio- and enantioselective amination of acyclic branched α-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates α-hydrazido-α-alkynyl ketone products with high enantioselectivity. Control experiments indicate that the α-alkynyl group in the ketone substrate is critical for both the reactivity and stereoselectivity of the reaction. Facile derivatizations of the functional group-abundant chiral product further highlight the value of this approach in the asymmetric synthesis of α-tertiary amines and N-containing heterocycles.</description><subject>Amination</subject><subject>Amines</subject><subject>Asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Enantiomers</subject><subject>Functional groups</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>Phosphoric acid</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNUN1KwzAYLaLgmLvxCQLeCdUkbZPWO5m_MByKXpc0-TqzdcmWpEJfwnfxRXwmI1P06hzOOd_H4STJMcFnBGfV-RV5nGPMKZ7uJSOKC5rmhFb7__hhMvF-iTEmtGC44KPk_QkW2qZIGIXACBO09dCBDPoNkFhrI6JikG2RkIPstESNE0a-gkKfH6noVoMZOrSCYA34CyT8sF5DcDEnrfHB9fL3_iGNShDaaLNA214EcEa4AflIwEowEf1RctCKzsPkB8fJy8318_Qunc1v76eXs1TSkoSUVaSBUlVEYokzllccU6VokXMlhGxymrecESZF3siSZ6zNoFAZBSaipRqejZOT3d-Ns9sefKiXto99Ol_TgrMyY0XOYup0l5LOeu-grTdOr2PpmuD6e_L6b_LsC0nQd1Y</recordid><startdate>20211007</startdate><enddate>20211007</enddate><creator>He, Faqian</creator><creator>Wang, Jiawen</creator><creator>Zhou, Fang</creator><creator>Tao, Houchao</creator><creator>Yang, Xiaoyu</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-0756-0671</orcidid><orcidid>https://orcid.org/0000-0001-7598-0275</orcidid></search><sort><creationdate>20211007</creationdate><title>Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters</title><author>He, Faqian ; Wang, Jiawen ; Zhou, Fang ; Tao, Houchao ; Yang, Xiaoyu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-691be8d91c0c03649702dd2547daacb424f7616ca4bc8736f3e5d32e6a424db73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amination</topic><topic>Amines</topic><topic>Asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Enantiomers</topic><topic>Functional groups</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>Phosphoric acid</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Faqian</creatorcontrib><creatorcontrib>Wang, Jiawen</creatorcontrib><creatorcontrib>Zhou, Fang</creatorcontrib><creatorcontrib>Tao, Houchao</creatorcontrib><creatorcontrib>Yang, Xiaoyu</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Faqian</au><au>Wang, Jiawen</au><au>Zhou, Fang</au><au>Tao, Houchao</au><au>Yang, Xiaoyu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-10-07</date><risdate>2021</risdate><volume>8</volume><issue>19</issue><spage>5377</spage><epage>5382</epage><pages>5377-5382</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>The direct regio- and enantioselective amination of acyclic branched α-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates α-hydrazido-α-alkynyl ketone products with high enantioselectivity. 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| ispartof | Organic Chemistry Frontiers, 2021-10, Vol.8 (19), p.5377-5382 |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Amination Amines Asymmetric synthesis Asymmetry Catalysis Enantiomers Functional groups Ketones Organic chemistry Phosphoric acid Stereoselectivity Substrates |
| title | Regio- and enantioselective amination of acyclic branched α-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters |
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