Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers
A novel four-component diastereoselective synthesis of polysubstituted 2-piperidinones is reported. The Michael addition–Mannich cascade of benzylidenemalononitriles or benzylidenecyanoacetates, dialkyl malonates, aromatic aldehydes and ammonium acetate in alcohols provides convenient access to alky...
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| Veröffentlicht in: | Research on chemical intermediates 2020-02, Vol.46 (2), p.1183-1199 |
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| creator | Vereshchagin, Anatoly N. Karpenko, Kirill A. Elinson, Michail N. Goloveshkin, Alexander S. Dorofeeva, Evgeniya O. Egorov, Mikhail P. |
| description | A novel four-component diastereoselective synthesis of polysubstituted 2-piperidinones is reported. The Michael addition–Mannich cascade of benzylidenemalononitriles or benzylidenecyanoacetates, dialkyl malonates, aromatic aldehydes and ammonium acetate in alcohols provides convenient access to alkyl (±)-5,5-dicyano-2-oxo-4,6-diarylpiperidine-3-carboxylates with three stereocenters in 66–92% or dialkyl (±)-2,4-diaryl-3-cyano-6-oxopiperidine-3,5-dicarboxylates with four stereocenters in 62–90%. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by
1
H NMR,
13
C NMR, IR, elemental analysis and mass spectral studies. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.
Graphic abstract |
| doi_str_mv | 10.1007/s11164-019-04027-4 |
| format | Article |
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1
H NMR,
13
C NMR, IR, elemental analysis and mass spectral studies. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.
Graphic abstract</description><identifier>ISSN: 0922-6168</identifier><identifier>EISSN: 1568-5675</identifier><identifier>DOI: 10.1007/s11164-019-04027-4</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Alcohols ; Aldehydes ; Ammonium acetate ; Carboxylates ; Catalysis ; Chemical analysis ; Chemistry ; Chemistry and Materials Science ; Infrared analysis ; Inorganic Chemistry ; NMR ; Nuclear magnetic resonance ; Physical Chemistry ; Stereoselectivity ; Synthesis</subject><ispartof>Research on chemical intermediates, 2020-02, Vol.46 (2), p.1183-1199</ispartof><rights>Springer Nature B.V. 2019</rights><rights>2019© Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-872fa1a8c4b07432d2b6252f8683d202bd008935d7f17fe257c87dfb1e3c29c23</citedby><cites>FETCH-LOGICAL-c356t-872fa1a8c4b07432d2b6252f8683d202bd008935d7f17fe257c87dfb1e3c29c23</cites><orcidid>0000-0001-8675-4943</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11164-019-04027-4$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11164-019-04027-4$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,41486,42555,51317</link.rule.ids></links><search><creatorcontrib>Vereshchagin, Anatoly N.</creatorcontrib><creatorcontrib>Karpenko, Kirill A.</creatorcontrib><creatorcontrib>Elinson, Michail N.</creatorcontrib><creatorcontrib>Goloveshkin, Alexander S.</creatorcontrib><creatorcontrib>Dorofeeva, Evgeniya O.</creatorcontrib><creatorcontrib>Egorov, Mikhail P.</creatorcontrib><title>Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers</title><title>Research on chemical intermediates</title><addtitle>Res Chem Intermed</addtitle><description>A novel four-component diastereoselective synthesis of polysubstituted 2-piperidinones is reported. The Michael addition–Mannich cascade of benzylidenemalononitriles or benzylidenecyanoacetates, dialkyl malonates, aromatic aldehydes and ammonium acetate in alcohols provides convenient access to alkyl (±)-5,5-dicyano-2-oxo-4,6-diarylpiperidine-3-carboxylates with three stereocenters in 66–92% or dialkyl (±)-2,4-diaryl-3-cyano-6-oxopiperidine-3,5-dicarboxylates with four stereocenters in 62–90%. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by
1
H NMR,
13
C NMR, IR, elemental analysis and mass spectral studies. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.
Graphic abstract</description><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Ammonium acetate</subject><subject>Carboxylates</subject><subject>Catalysis</subject><subject>Chemical analysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Infrared analysis</subject><subject>Inorganic Chemistry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Physical Chemistry</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLxDAURoMoOI7-AVcB19E8miZdivgCwY2uQ5vczETGtuZmlFn4361WcOcqm_OdGw4hp4KfC87NBQoh6opx0TBecWlYtUcWQteW6drofbLgjZSsFrU9JEeIL5wLbS1fkM-7tFpvdjSkFgtkGBA24Et6BxqHbWZ-eB2HHvpCcdeXNWBCOkQ6DpsdbjssqWwLBCrZmEbIKaR-opF-pLKmZZ0BaNuHHxWd_Svok6d-MkLGY3IQ2w3Cye-7JM83109Xd-zh8fb-6vKBeaXrwqyRsRWt9VXHTaVkkF0ttYy2tipILrvAuW2UDiYKE0Fq460JsROgvGy8VEtyNnvHPLxtAYt7mX7UTyedVJXSVqiqmSg5Uz4PiBmiG3N6bfPOCe6-M7s5s5syu5_MrppGah7hBPcryH_qf1ZflXiDTQ</recordid><startdate>20200201</startdate><enddate>20200201</enddate><creator>Vereshchagin, Anatoly N.</creator><creator>Karpenko, Kirill A.</creator><creator>Elinson, Michail N.</creator><creator>Goloveshkin, Alexander S.</creator><creator>Dorofeeva, Evgeniya O.</creator><creator>Egorov, Mikhail P.</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8675-4943</orcidid></search><sort><creationdate>20200201</creationdate><title>Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers</title><author>Vereshchagin, Anatoly N. ; Karpenko, Kirill A. ; Elinson, Michail N. ; Goloveshkin, Alexander S. ; Dorofeeva, Evgeniya O. ; Egorov, Mikhail P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-872fa1a8c4b07432d2b6252f8683d202bd008935d7f17fe257c87dfb1e3c29c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Ammonium acetate</topic><topic>Carboxylates</topic><topic>Catalysis</topic><topic>Chemical analysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Infrared analysis</topic><topic>Inorganic Chemistry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Physical Chemistry</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vereshchagin, Anatoly N.</creatorcontrib><creatorcontrib>Karpenko, Kirill A.</creatorcontrib><creatorcontrib>Elinson, Michail N.</creatorcontrib><creatorcontrib>Goloveshkin, Alexander S.</creatorcontrib><creatorcontrib>Dorofeeva, Evgeniya O.</creatorcontrib><creatorcontrib>Egorov, Mikhail P.</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vereshchagin, Anatoly N.</au><au>Karpenko, Kirill A.</au><au>Elinson, Michail N.</au><au>Goloveshkin, Alexander S.</au><au>Dorofeeva, Evgeniya O.</au><au>Egorov, Mikhail P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2020-02-01</date><risdate>2020</risdate><volume>46</volume><issue>2</issue><spage>1183</spage><epage>1199</epage><pages>1183-1199</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>A novel four-component diastereoselective synthesis of polysubstituted 2-piperidinones is reported. The Michael addition–Mannich cascade of benzylidenemalononitriles or benzylidenecyanoacetates, dialkyl malonates, aromatic aldehydes and ammonium acetate in alcohols provides convenient access to alkyl (±)-5,5-dicyano-2-oxo-4,6-diarylpiperidine-3-carboxylates with three stereocenters in 66–92% or dialkyl (±)-2,4-diaryl-3-cyano-6-oxopiperidine-3,5-dicarboxylates with four stereocenters in 62–90%. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by
1
H NMR,
13
C NMR, IR, elemental analysis and mass spectral studies. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.
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| subjects | Alcohols Aldehydes Ammonium acetate Carboxylates Catalysis Chemical analysis Chemistry Chemistry and Materials Science Infrared analysis Inorganic Chemistry NMR Nuclear magnetic resonance Physical Chemistry Stereoselectivity Synthesis |
| title | Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers |
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