Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction
An NHC‐catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones. This methodology offers an efficient and rapid access to a wide range of...
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| Veröffentlicht in: | Chemistry : a European journal 2018-02, Vol.24 (9), p.2103-2108 |
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| container_issue | 9 |
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| container_title | Chemistry : a European journal |
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| creator | Fang, Chao Cao, Jing Sun, Kewen Zhu, Jindong Lu, Tao Du, Ding |
| description | An NHC‐catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N‐functionalization to afford diverse N‐substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.
Get selective! An N‐heterocyclic carbene catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones (see scheme). |
| doi_str_mv | 10.1002/chem.201705050 |
| format | Article |
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Get selective! An N‐heterocyclic carbene catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201705050</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>annulation ; Aromatic compounds ; asymmetric synthesis ; benzodiazepinone ; carbenes ; Chemical reactions ; Chemical synthesis ; Chemistry ; Diamines ; Enantiomers ; Organic chemistry ; unsaturated acylazolium</subject><ispartof>Chemistry : a European journal, 2018-02, Vol.24 (9), p.2103-2108</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3870-e59e935584cbea2bfac8e4ee5713b96c58f2c74c36a4205ec48532a9407387573</citedby><cites>FETCH-LOGICAL-c3870-e59e935584cbea2bfac8e4ee5713b96c58f2c74c36a4205ec48532a9407387573</cites><orcidid>0000-0002-4615-5433</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.201705050$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201705050$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Fang, Chao</creatorcontrib><creatorcontrib>Cao, Jing</creatorcontrib><creatorcontrib>Sun, Kewen</creatorcontrib><creatorcontrib>Zhu, Jindong</creatorcontrib><creatorcontrib>Lu, Tao</creatorcontrib><creatorcontrib>Du, Ding</creatorcontrib><title>Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction</title><title>Chemistry : a European journal</title><description>An NHC‐catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N‐functionalization to afford diverse N‐substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.
Get selective! An N‐heterocyclic carbene catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones (see scheme).</description><subject>annulation</subject><subject>Aromatic compounds</subject><subject>asymmetric synthesis</subject><subject>benzodiazepinone</subject><subject>carbenes</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Diamines</subject><subject>Enantiomers</subject><subject>Organic chemistry</subject><subject>unsaturated acylazolium</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkUtrGzEURkVJoY7bbdeCbgLpuHqORsvEceJA2kIfq1IGjXyHKIwlRxo3jFdZZhm66f_LL6mMSwLZFCHulTjnSvAh9JaSCSWEfbCXsJwwQhWReb1AIyoZLbgq5R4aES1UUUquX6H9lK4IIbrkfIT-nLgItsfGL_DMG9-7kKDLN-4X4K-D7y8huYRDiz893P2eP9zen0YATN_L3B6D34SFMxtYOZ_PLO_gIeFmyAOzcXs_hx5isIPtnMVTExvwkGtvumEDC_yDH4qf-Mj7dWfy0x5_AWO3zWv0sjVdgjf_6hh9P519m86Li89n59Oji8LySpECpAbNpayEbcCwpjW2AgEgFeWNLq2sWmaVsLw0ghEJVlSSM6MFUdmXio_RwW7uKobrNaS-XrpkoeuMh7BONdWqFIJzpTP67hl6FdbR599lSmtJaaVYpiY7ysaQUoS2XkW3NHGoKam3OdXbnOrHnLKgd8KN62D4D11P57OPT-5fjCucdw</recordid><startdate>20180209</startdate><enddate>20180209</enddate><creator>Fang, Chao</creator><creator>Cao, Jing</creator><creator>Sun, Kewen</creator><creator>Zhu, Jindong</creator><creator>Lu, Tao</creator><creator>Du, Ding</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/0000-0002-4615-5433</orcidid></search><sort><creationdate>20180209</creationdate><title>Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction</title><author>Fang, Chao ; Cao, Jing ; Sun, Kewen ; Zhu, Jindong ; Lu, Tao ; Du, Ding</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3870-e59e935584cbea2bfac8e4ee5713b96c58f2c74c36a4205ec48532a9407387573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>annulation</topic><topic>Aromatic compounds</topic><topic>asymmetric synthesis</topic><topic>benzodiazepinone</topic><topic>carbenes</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Diamines</topic><topic>Enantiomers</topic><topic>Organic chemistry</topic><topic>unsaturated acylazolium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fang, Chao</creatorcontrib><creatorcontrib>Cao, Jing</creatorcontrib><creatorcontrib>Sun, Kewen</creatorcontrib><creatorcontrib>Zhu, Jindong</creatorcontrib><creatorcontrib>Lu, Tao</creatorcontrib><creatorcontrib>Du, Ding</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>Fang, Chao</au><au>Cao, Jing</au><au>Sun, Kewen</au><au>Zhu, Jindong</au><au>Lu, Tao</au><au>Du, Ding</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction</atitle><jtitle>Chemistry : a European journal</jtitle><date>2018-02-09</date><risdate>2018</risdate><volume>24</volume><issue>9</issue><spage>2103</spage><epage>2108</epage><pages>2103-2108</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>An NHC‐catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N‐functionalization to afford diverse N‐substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.
Get selective! An N‐heterocyclic carbene catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones (see scheme).</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.201705050</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-4615-5433</orcidid></addata></record> |
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| subjects | annulation Aromatic compounds asymmetric synthesis benzodiazepinone carbenes Chemical reactions Chemical synthesis Chemistry Diamines Enantiomers Organic chemistry unsaturated acylazolium |
| title | Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction |
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