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Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts
The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral N , N , P -ligands. This method features a broad substrate scope and wide functional group tolerance, generating...
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| Published in: | Chemical communications (Cambridge, England) England), 2021-05, Vol.57 (38), p.4674-4677 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c337t-a74c8d2bb87c89f50dcb88510b343b978af2a59028f9ce8423619ddc27c018b43 |
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| cites | cdi_FETCH-LOGICAL-c337t-a74c8d2bb87c89f50dcb88510b343b978af2a59028f9ce8423619ddc27c018b43 |
| container_end_page | 4677 |
| container_issue | 38 |
| container_start_page | 4674 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 57 |
| creator | Huang, Jian Kong, Han-Han Li, Si-Jia Zhang, Rui-Jin Qian, Hao-Dong Li, Dan-Ran He, Jin-Yu Zheng, Yi-Nuo Xu, Hao |
| description | The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral
N
,
N
,
P
-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.
A highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized under mild conditions. |
| doi_str_mv | 10.1039/d1cc00663k |
| format | article |
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N
,
N
,
P
-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.
A highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized under mild conditions.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc00663k</identifier><identifier>PMID: 33977976</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Amines ; Copper ; Crystallography ; Enantiomers ; Esters ; Functional groups ; NMR ; Nuclear magnetic resonance ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2021-05, Vol.57 (38), p.4674-4677</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-a74c8d2bb87c89f50dcb88510b343b978af2a59028f9ce8423619ddc27c018b43</citedby><cites>FETCH-LOGICAL-c337t-a74c8d2bb87c89f50dcb88510b343b978af2a59028f9ce8423619ddc27c018b43</cites><orcidid>0000-0001-9685-7364</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33977976$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Jian</creatorcontrib><creatorcontrib>Kong, Han-Han</creatorcontrib><creatorcontrib>Li, Si-Jia</creatorcontrib><creatorcontrib>Zhang, Rui-Jin</creatorcontrib><creatorcontrib>Qian, Hao-Dong</creatorcontrib><creatorcontrib>Li, Dan-Ran</creatorcontrib><creatorcontrib>He, Jin-Yu</creatorcontrib><creatorcontrib>Zheng, Yi-Nuo</creatorcontrib><creatorcontrib>Xu, Hao</creatorcontrib><title>Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral
N
,
N
,
P
-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.
A highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized under mild conditions.</description><subject>Amines</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Enantiomers</subject><subject>Esters</subject><subject>Functional groups</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLxDAQB_AgiruuXrwrBS8iVJMmaZLjUp-4oAcFbyVNUrdrXyYtUj-92YcrmEsyzI9h-AeAYwQvEcTiSiOlIIxj_LEDxgjHJKSEv-0u31SEDBM6AgfOLaA_iPJ9MMJYMCZYPAbPUzdUlelsoQLVtK2xoZKdLIdvo4PWNq2070Ppm7IqatkVTR18Fd18VZpgPmjbqHnZ2EKbwMmyc4dgL5elM0ebewJeb29ekvtw9nT3kExnocKYdaFkRHEdZRlnioucQq0yzimCGSY4E4zLPJJUwIjnQhlOIhwjobWKmIKIZwRPwPl6rl_yszeuS6vCKVOWsjZN79KIRrHPAjLo6dk_umh6W_vtlopwzGDMvLpYK2Ub56zJ09YWlbRDimC6zDm9RkmyyvnR49PNyD6rjN7S32A9OFkD69S2-_dR-AdfRoJO</recordid><startdate>20210511</startdate><enddate>20210511</enddate><creator>Huang, Jian</creator><creator>Kong, Han-Han</creator><creator>Li, Si-Jia</creator><creator>Zhang, Rui-Jin</creator><creator>Qian, Hao-Dong</creator><creator>Li, Dan-Ran</creator><creator>He, Jin-Yu</creator><creator>Zheng, Yi-Nuo</creator><creator>Xu, Hao</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9685-7364</orcidid></search><sort><creationdate>20210511</creationdate><title>Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts</title><author>Huang, Jian ; Kong, Han-Han ; Li, Si-Jia ; Zhang, Rui-Jin ; Qian, Hao-Dong ; Li, Dan-Ran ; He, Jin-Yu ; Zheng, Yi-Nuo ; Xu, Hao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-a74c8d2bb87c89f50dcb88510b343b978af2a59028f9ce8423619ddc27c018b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amines</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Enantiomers</topic><topic>Esters</topic><topic>Functional groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Jian</creatorcontrib><creatorcontrib>Kong, Han-Han</creatorcontrib><creatorcontrib>Li, Si-Jia</creatorcontrib><creatorcontrib>Zhang, Rui-Jin</creatorcontrib><creatorcontrib>Qian, Hao-Dong</creatorcontrib><creatorcontrib>Li, Dan-Ran</creatorcontrib><creatorcontrib>He, Jin-Yu</creatorcontrib><creatorcontrib>Zheng, Yi-Nuo</creatorcontrib><creatorcontrib>Xu, Hao</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Jian</au><au>Kong, Han-Han</au><au>Li, Si-Jia</au><au>Zhang, Rui-Jin</au><au>Qian, Hao-Dong</au><au>Li, Dan-Ran</au><au>He, Jin-Yu</au><au>Zheng, Yi-Nuo</au><au>Xu, Hao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-05-11</date><risdate>2021</risdate><volume>57</volume><issue>38</issue><spage>4674</spage><epage>4677</epage><pages>4674-4677</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral
N
,
N
,
P
-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.
A highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized under mild conditions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33977976</pmid><doi>10.1039/d1cc00663k</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-9685-7364</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2021-05, Vol.57 (38), p.4674-4677 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_journals_2524837067 |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Amines Copper Crystallography Enantiomers Esters Functional groups NMR Nuclear magnetic resonance Substrates |
| title | Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts |
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