Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides
The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizati...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-06, Vol.56 (27), p.7958-7962 |
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| creator | Tong, Shuo Piemontesi, Cyril Wang, Qian Wang, Mei‐Xiang Zhu, Jieping |
| description | The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three‐component reaction with isocyanides and carboxylic acids to afford functionalized N‐acyl proline amides. High diastereoselectivity was observed in the synthesis of 4‐alkoxy and 4,5‐disubstituted proline derivatives. This work represents the first examples of a three‐component cyclizative 1,1‐aminoacylation of terminal alkynes.
No atom lost: Homopropargylamines react with isocyanides and either carboxylic acids or water in the presence of a catalytic amount of silver acetate to afford substituted proline amides. This three‐component reaction proceeds by a cyclizative 1,1‐aminoacylation of terminal alkynes and affords good to excellent yields. Boc=tert‐butoxycarbonyl. |
| doi_str_mv | 10.1002/anie.201704727 |
| format | Article |
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No atom lost: Homopropargylamines react with isocyanides and either carboxylic acids or water in the presence of a catalytic amount of silver acetate to afford substituted proline amides. This three‐component reaction proceeds by a cyclizative 1,1‐aminoacylation of terminal alkynes and affords good to excellent yields. Boc=tert‐butoxycarbonyl.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201704727</identifier><identifier>PMID: 28493495</identifier><language>eng</language><publisher>Germany</publisher><subject>alkynes ; heterocycles ; isocyanides ; multicomponent reactions ; silver</subject><ispartof>Angewandte Chemie International Edition, 2017-06, Vol.56 (27), p.7958-7962</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3457-47bebe7d98d62be3b97683ddf8a42002546107a071808028ce38882d472d5cef3</citedby><cites>FETCH-LOGICAL-c3457-47bebe7d98d62be3b97683ddf8a42002546107a071808028ce38882d472d5cef3</cites><orcidid>0000-0002-8390-6689</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%2Fanie.201704727$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201704727$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28493495$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tong, Shuo</creatorcontrib><creatorcontrib>Piemontesi, Cyril</creatorcontrib><creatorcontrib>Wang, Qian</creatorcontrib><creatorcontrib>Wang, Mei‐Xiang</creatorcontrib><creatorcontrib>Zhu, Jieping</creatorcontrib><title>Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three‐component reaction with isocyanides and carboxylic acids to afford functionalized N‐acyl proline amides. High diastereoselectivity was observed in the synthesis of 4‐alkoxy and 4,5‐disubstituted proline derivatives. This work represents the first examples of a three‐component cyclizative 1,1‐aminoacylation of terminal alkynes.
No atom lost: Homopropargylamines react with isocyanides and either carboxylic acids or water in the presence of a catalytic amount of silver acetate to afford substituted proline amides. This three‐component reaction proceeds by a cyclizative 1,1‐aminoacylation of terminal alkynes and affords good to excellent yields. Boc=tert‐butoxycarbonyl.</description><subject>alkynes</subject><subject>heterocycles</subject><subject>isocyanides</subject><subject>multicomponent reactions</subject><subject>silver</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkLtOwzAUhi0E4r4yIo8MpNixUztspeJSCcFAmSMnPoGAExc7BYWJmYlX4UV4CJ4ER-UyMtk-_vzL_4fQDiUDSkh8oJoKBjGhgnARiyW0TpOYRkwIthz2nLFIyISuoQ3v7wIvJRmuorVY8pTxNFlHr1eVeQT3-fI2Vq0y3TNoPL11AP3E1jPbQNNiuk_DeVRXjVVFZ1Rb2QbbEp_Z2s6cnSl3E6bhGvwh_njvWa2rnvK4tA4f2fYWT8EFQhk8MvddILFqNJ54W3ShhAa_hVZKZTxsf6-b6PrkeDo-i84vTyfj0XlUMJ6IiIscchA6lXoY58DyVAwl07qUisehYsKHlAhFBJVEhsYFMCllrIMfnRRQsk20t8gNP3-Yg2-zuvIFGKMasHOfUZkKSRLO0oAOFmjhrPcOymzmqlq5LqMk6_1nvf_s1394sPudPc9r0L_4j_AApAvgqTLQ_ROXjS4mx3_hX9u0mDk</recordid><startdate>20170626</startdate><enddate>20170626</enddate><creator>Tong, Shuo</creator><creator>Piemontesi, Cyril</creator><creator>Wang, Qian</creator><creator>Wang, Mei‐Xiang</creator><creator>Zhu, Jieping</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8390-6689</orcidid></search><sort><creationdate>20170626</creationdate><title>Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides</title><author>Tong, Shuo ; Piemontesi, Cyril ; Wang, Qian ; Wang, Mei‐Xiang ; Zhu, Jieping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3457-47bebe7d98d62be3b97683ddf8a42002546107a071808028ce38882d472d5cef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>alkynes</topic><topic>heterocycles</topic><topic>isocyanides</topic><topic>multicomponent reactions</topic><topic>silver</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tong, Shuo</creatorcontrib><creatorcontrib>Piemontesi, Cyril</creatorcontrib><creatorcontrib>Wang, Qian</creatorcontrib><creatorcontrib>Wang, Mei‐Xiang</creatorcontrib><creatorcontrib>Zhu, Jieping</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tong, Shuo</au><au>Piemontesi, Cyril</au><au>Wang, Qian</au><au>Wang, Mei‐Xiang</au><au>Zhu, Jieping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-06-26</date><risdate>2017</risdate><volume>56</volume><issue>27</issue><spage>7958</spage><epage>7962</epage><pages>7958-7962</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three‐component reaction with isocyanides and carboxylic acids to afford functionalized N‐acyl proline amides. High diastereoselectivity was observed in the synthesis of 4‐alkoxy and 4,5‐disubstituted proline derivatives. This work represents the first examples of a three‐component cyclizative 1,1‐aminoacylation of terminal alkynes.
No atom lost: Homopropargylamines react with isocyanides and either carboxylic acids or water in the presence of a catalytic amount of silver acetate to afford substituted proline amides. This three‐component reaction proceeds by a cyclizative 1,1‐aminoacylation of terminal alkynes and affords good to excellent yields. Boc=tert‐butoxycarbonyl.</abstract><cop>Germany</cop><pmid>28493495</pmid><doi>10.1002/anie.201704727</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8390-6689</orcidid></addata></record> |
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| subjects | alkynes heterocycles isocyanides multicomponent reactions silver |
| title | Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides |
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