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Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification
An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflec...
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| Published in: | Angewandte Chemie International Edition 2018-05, Vol.57 (19), p.5384-5388 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c4761-80f7bd67bd0976cb80e07fbc23560b4108cced5caea1159e1cf04c0d805680093 |
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| cites | cdi_FETCH-LOGICAL-c4761-80f7bd67bd0976cb80e07fbc23560b4108cced5caea1159e1cf04c0d805680093 |
| container_end_page | 5388 |
| container_issue | 19 |
| container_start_page | 5384 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Liang, Yu‐Feng Steinbock, Ralf Münch, Annika Stalke, Dietmar Ackermann, Lutz |
| description | An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free conditions of a wealth of marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.
Smart Man: An inexpensive, nontoxic manganese complex catalyzed carbonylative alkyne annulation reactions to form pyrido[1,2‐a]pyrimidin‐4‐ones under ambient pressure. The manganese catalyst outperformed other typically used metal catalysts and showed outstanding versatility, as reflected by the modification of various marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates. |
| doi_str_mv | 10.1002/anie.201801111 |
| format | article |
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Smart Man: An inexpensive, nontoxic manganese complex catalyzed carbonylative alkyne annulation reactions to form pyrido[1,2‐a]pyrimidin‐4‐ones under ambient pressure. The manganese catalyst outperformed other typically used metal catalysts and showed outstanding versatility, as reflected by the modification of various marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201801111</identifier><identifier>PMID: 29474755</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkaloids ; Amino acids ; annulation ; Carbohydrates ; carbonylation ; Carbonyls ; Catalysis ; Catalysts ; late-stage modification ; Manganese ; Natural products ; Pressure ; Racemization ; Steroid hormones ; Steroids ; Substrates ; traceless directing groups</subject><ispartof>Angewandte Chemie International Edition, 2018-05, Vol.57 (19), p.5384-5388</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-c4761-80f7bd67bd0976cb80e07fbc23560b4108cced5caea1159e1cf04c0d805680093</citedby><cites>FETCH-LOGICAL-c4761-80f7bd67bd0976cb80e07fbc23560b4108cced5caea1159e1cf04c0d805680093</cites><orcidid>0000-0001-7034-8772</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/29474755$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liang, Yu‐Feng</creatorcontrib><creatorcontrib>Steinbock, Ralf</creatorcontrib><creatorcontrib>Münch, Annika</creatorcontrib><creatorcontrib>Stalke, Dietmar</creatorcontrib><creatorcontrib>Ackermann, Lutz</creatorcontrib><title>Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free conditions of a wealth of marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.
Smart Man: An inexpensive, nontoxic manganese complex catalyzed carbonylative alkyne annulation reactions to form pyrido[1,2‐a]pyrimidin‐4‐ones under ambient pressure. The manganese catalyst outperformed other typically used metal catalysts and showed outstanding versatility, as reflected by the modification of various marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.</description><subject>Alkaloids</subject><subject>Amino acids</subject><subject>annulation</subject><subject>Carbohydrates</subject><subject>carbonylation</subject><subject>Carbonyls</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>late-stage modification</subject><subject>Manganese</subject><subject>Natural products</subject><subject>Pressure</subject><subject>Racemization</subject><subject>Steroid hormones</subject><subject>Steroids</subject><subject>Substrates</subject><subject>traceless directing groups</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OwzAQhC0EolC4ckSROKes82fnWJUClUqR-DkHx9lUqVKn2AkQTjwCz8iT4NBSjqy02jl8MysNIScUBhTAOxeqwIEHlAO1s0MOaOhR12fM37U68H2X8ZD2yKExC8tzDtE-6XlxwAIWhgfk6UaouVBo8OvjcyRqUbbvmDkjodNKtaWoixd0hko1nayUcfJKO3eYVW-Wn2FTa1E6U1F39vtazNG5sA5tiryQP44jspeL0uDx5vbJ4-X4YXTtTm-vJqPh1JUBi6jLIWdpFtmFmEUy5YDA8lR6fhhBGlDgUmIWSoGC0jBGKnMIJGQcwogDxH6fnK1zV7p6btDUyaJqtLIvEw986nuWYZYarCmpK2M05slKF0uh24RC0hWadIUm20Kt4XQT26RLzLb4b4MWiNfAa1Fi-09cMpxNxn_h3_QPhdE</recordid><startdate>20180504</startdate><enddate>20180504</enddate><creator>Liang, Yu‐Feng</creator><creator>Steinbock, Ralf</creator><creator>Münch, Annika</creator><creator>Stalke, Dietmar</creator><creator>Ackermann, Lutz</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><orcidid>https://orcid.org/0000-0001-7034-8772</orcidid></search><sort><creationdate>20180504</creationdate><title>Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification</title><author>Liang, Yu‐Feng ; Steinbock, Ralf ; Münch, Annika ; Stalke, Dietmar ; Ackermann, Lutz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4761-80f7bd67bd0976cb80e07fbc23560b4108cced5caea1159e1cf04c0d805680093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkaloids</topic><topic>Amino acids</topic><topic>annulation</topic><topic>Carbohydrates</topic><topic>carbonylation</topic><topic>Carbonyls</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>late-stage modification</topic><topic>Manganese</topic><topic>Natural products</topic><topic>Pressure</topic><topic>Racemization</topic><topic>Steroid hormones</topic><topic>Steroids</topic><topic>Substrates</topic><topic>traceless directing groups</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liang, Yu‐Feng</creatorcontrib><creatorcontrib>Steinbock, Ralf</creatorcontrib><creatorcontrib>Münch, Annika</creatorcontrib><creatorcontrib>Stalke, Dietmar</creatorcontrib><creatorcontrib>Ackermann, Lutz</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liang, Yu‐Feng</au><au>Steinbock, Ralf</au><au>Münch, Annika</au><au>Stalke, Dietmar</au><au>Ackermann, Lutz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-05-04</date><risdate>2018</risdate><volume>57</volume><issue>19</issue><spage>5384</spage><epage>5388</epage><pages>5384-5388</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free conditions of a wealth of marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.
Smart Man: An inexpensive, nontoxic manganese complex catalyzed carbonylative alkyne annulation reactions to form pyrido[1,2‐a]pyrimidin‐4‐ones under ambient pressure. The manganese catalyst outperformed other typically used metal catalysts and showed outstanding versatility, as reflected by the modification of various marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29474755</pmid><doi>10.1002/anie.201801111</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-7034-8772</orcidid></addata></record> |
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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-05, Vol.57 (19), p.5384-5388 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_journals_2031320937 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alkaloids Amino acids annulation Carbohydrates carbonylation Carbonyls Catalysis Catalysts late-stage modification Manganese Natural products Pressure Racemization Steroid hormones Steroids Substrates traceless directing groups |
| title | Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification |
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