Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction
An asymmetric decarboxylative Mannich reaction of phosphonate sultam‐ketimines with malonic acid half esters is developed enabled by saccharide‐derived bifunctional amino thiourea catalysis. This protocol provides access to a broad range of α‐amino‐β‐carboxylic phosphonates featuring the N,P‐contain...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2022-06, Vol.364 (11), p.1908-1912 |
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| container_end_page | 1912 |
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| container_issue | 11 |
| container_start_page | 1908 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 364 |
| creator | Wang, Xue‐Qi Feng, Fang‐Fang Nie, Jing Zhang, Fa‐Guang Ma, Jun‐An |
| description | An asymmetric decarboxylative Mannich reaction of phosphonate sultam‐ketimines with malonic acid half esters is developed enabled by saccharide‐derived bifunctional amino thiourea catalysis. This protocol provides access to a broad range of α‐amino‐β‐carboxylic phosphonates featuring the N,P‐containing tetrasubstituted stereocenters with 78–99% ee. Further synthetic derivatizations could allow the introduction of amide, alcohol, and azetidine scaffolds to the core structures. |
| doi_str_mv | 10.1002/adsc.202200306 |
| format | Article |
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This protocol provides access to a broad range of α‐amino‐β‐carboxylic phosphonates featuring the N,P‐containing tetrasubstituted stereocenters with 78–99% ee. Further synthetic derivatizations could allow the introduction of amide, alcohol, and azetidine scaffolds to the core structures.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202200306</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Aminophosphonates ; Carbohydrates ; Cyclic Ketimines ; Decarboxylative Mannich Reaction ; Enantiomers ; Enantioselectivity ; Esters ; Imines ; Phosphonates ; Phosphonic acids ; Thiourea ; Thioureas</subject><ispartof>Advanced synthesis & catalysis, 2022-06, Vol.364 (11), p.1908-1912</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2476-e0a90656cebeb10a75280f2dc4a0a9368197a34b11082ca013fed73ccb76b89e3</citedby><cites>FETCH-LOGICAL-c2476-e0a90656cebeb10a75280f2dc4a0a9368197a34b11082ca013fed73ccb76b89e3</cites><orcidid>0000-0002-0251-0456</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%2Fadsc.202200306$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202200306$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Wang, Xue‐Qi</creatorcontrib><creatorcontrib>Feng, Fang‐Fang</creatorcontrib><creatorcontrib>Nie, Jing</creatorcontrib><creatorcontrib>Zhang, Fa‐Guang</creatorcontrib><creatorcontrib>Ma, Jun‐An</creatorcontrib><title>Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction</title><title>Advanced synthesis & catalysis</title><description>An asymmetric decarboxylative Mannich reaction of phosphonate sultam‐ketimines with malonic acid half esters is developed enabled by saccharide‐derived bifunctional amino thiourea catalysis. 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Further synthetic derivatizations could allow the introduction of amide, alcohol, and azetidine scaffolds to the core structures.</description><subject>Aminophosphonates</subject><subject>Carbohydrates</subject><subject>Cyclic Ketimines</subject><subject>Decarboxylative Mannich Reaction</subject><subject>Enantiomers</subject><subject>Enantioselectivity</subject><subject>Esters</subject><subject>Imines</subject><subject>Phosphonates</subject><subject>Phosphonic acids</subject><subject>Thiourea</subject><subject>Thioureas</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkc1O3DAURqOqSKUD264tdT3DtZPYyXKUmUKlqUD8rKMb50YxCvHUzgBhxSP0BXg5nqQeZgRLVrbl75x7pS-KfnCYcQBxgrXXMwFCAMQgv0SHXPJ0mnCZf32_p_At-u79LQBXmVKH0cuyx34w1lNHejD3xArb-8FtwsP2zDZsfmd6ywp0lX0cO6Nfn_9dtNavW9sbzeba1GxBztzjlvYs-KqOalaNrGiNw24vuG6N3TjCgBc4YDc-0RbUe-8bzf5gH6QtuyR8m38UHTTYeTren5Po5tfyujibrs5Pfxfz1VSLRMkpAeYgU6mpoooDqlRk0IhaJxh-YpnxXGGcVJxDJjQCjxuqVax1pWSV5RRPop8779rZvxvyQ3kblu3DyFJIFafBLZKQmu1S2lnvHTXl2pk7dGPJodxWUG4rKN8rCEC-Ax5MR-Mn6XK-uCo-2P8FRJAJ</recordid><startdate>20220607</startdate><enddate>20220607</enddate><creator>Wang, Xue‐Qi</creator><creator>Feng, Fang‐Fang</creator><creator>Nie, Jing</creator><creator>Zhang, Fa‐Guang</creator><creator>Ma, Jun‐An</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-0251-0456</orcidid></search><sort><creationdate>20220607</creationdate><title>Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction</title><author>Wang, Xue‐Qi ; Feng, Fang‐Fang ; Nie, Jing ; Zhang, Fa‐Guang ; Ma, Jun‐An</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2476-e0a90656cebeb10a75280f2dc4a0a9368197a34b11082ca013fed73ccb76b89e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aminophosphonates</topic><topic>Carbohydrates</topic><topic>Cyclic Ketimines</topic><topic>Decarboxylative Mannich Reaction</topic><topic>Enantiomers</topic><topic>Enantioselectivity</topic><topic>Esters</topic><topic>Imines</topic><topic>Phosphonates</topic><topic>Phosphonic acids</topic><topic>Thiourea</topic><topic>Thioureas</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xue‐Qi</creatorcontrib><creatorcontrib>Feng, Fang‐Fang</creatorcontrib><creatorcontrib>Nie, Jing</creatorcontrib><creatorcontrib>Zhang, Fa‐Guang</creatorcontrib><creatorcontrib>Ma, Jun‐An</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Xue‐Qi</au><au>Feng, Fang‐Fang</au><au>Nie, Jing</au><au>Zhang, Fa‐Guang</au><au>Ma, Jun‐An</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2022-06-07</date><risdate>2022</risdate><volume>364</volume><issue>11</issue><spage>1908</spage><epage>1912</epage><pages>1908-1912</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An asymmetric decarboxylative Mannich reaction of phosphonate sultam‐ketimines with malonic acid half esters is developed enabled by saccharide‐derived bifunctional amino thiourea catalysis. 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| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2022-06, Vol.364 (11), p.1908-1912 |
| issn | 1615-4150 1615-4169 |
| language | eng |
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| source | Wiley Journals |
| subjects | Aminophosphonates Carbohydrates Cyclic Ketimines Decarboxylative Mannich Reaction Enantiomers Enantioselectivity Esters Imines Phosphonates Phosphonic acids Thiourea Thioureas |
| title | Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction |
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