Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes
Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl triazenes in the presence of a RuII catalyst with a chiral cyclopentadienyl ligand. These triazenes serve as unique vinyl cation surrogates. Under acidic conditions, the triazene functi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-09, Vol.56 (38), p.11490-11493 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Kossler, David Perrin, Florian G. Suleymanov, Abdusalom A. Kiefer, Gregor Scopelliti, Rosario Severin, Kay Cramer, Nicolai |
| description | Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl triazenes in the presence of a RuII catalyst with a chiral cyclopentadienyl ligand. These triazenes serve as unique vinyl cation surrogates. Under acidic conditions, the triazene functionality can be replaced with a variety of groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a pool of chiral polycyclic compounds.
In with the new, in with the Nu: 1‐Alkynyl triazenes and bicyclic alkenes underwent enantioselective [2+2] cycloaddition catalyzed by a chiral cyclopentadienyl RuII complex to give vinyl triazenes. The triazene functionality was readily replaced with a variety of nucleophiles, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a wide range of chiral polycyclic compounds. |
| doi_str_mv | 10.1002/anie.201706013 |
| format | Article |
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In with the new, in with the Nu: 1‐Alkynyl triazenes and bicyclic alkenes underwent enantioselective [2+2] cycloaddition catalyzed by a chiral cyclopentadienyl RuII complex to give vinyl triazenes. The triazene functionality was readily replaced with a variety of nucleophiles, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a wide range of chiral polycyclic compounds.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201706013</identifier><identifier>PMID: 28696574</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkenes ; Alkoxides ; Amides ; Aromatic compounds ; asymmetric catalysis ; Asymmetric synthesis ; Catalysts ; Cycloaddition ; divergent synthesis ; Enantiomers ; Halides ; Polycyclic compounds ; ruthenium ; triazenes</subject><ispartof>Angewandte Chemie International Edition, 2017-09, Vol.56 (38), p.11490-11493</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5163-6f033041ed4bfdfb0d847886feee47efc9de2dd617a38946fbc313fa3bde15db3</citedby><cites>FETCH-LOGICAL-c5163-6f033041ed4bfdfb0d847886feee47efc9de2dd617a38946fbc313fa3bde15db3</cites><orcidid>0000-0001-5740-8494 ; 0000-0003-2224-7234</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.201706013$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201706013$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28696574$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kossler, David</creatorcontrib><creatorcontrib>Perrin, Florian G.</creatorcontrib><creatorcontrib>Suleymanov, Abdusalom A.</creatorcontrib><creatorcontrib>Kiefer, Gregor</creatorcontrib><creatorcontrib>Scopelliti, Rosario</creatorcontrib><creatorcontrib>Severin, Kay</creatorcontrib><creatorcontrib>Cramer, Nicolai</creatorcontrib><title>Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl triazenes in the presence of a RuII catalyst with a chiral cyclopentadienyl ligand. These triazenes serve as unique vinyl cation surrogates. Under acidic conditions, the triazene functionality can be replaced with a variety of groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a pool of chiral polycyclic compounds.
In with the new, in with the Nu: 1‐Alkynyl triazenes and bicyclic alkenes underwent enantioselective [2+2] cycloaddition catalyzed by a chiral cyclopentadienyl RuII complex to give vinyl triazenes. 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These triazenes serve as unique vinyl cation surrogates. Under acidic conditions, the triazene functionality can be replaced with a variety of groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a pool of chiral polycyclic compounds.
In with the new, in with the Nu: 1‐Alkynyl triazenes and bicyclic alkenes underwent enantioselective [2+2] cycloaddition catalyzed by a chiral cyclopentadienyl RuII complex to give vinyl triazenes. The triazene functionality was readily replaced with a variety of nucleophiles, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a wide range of chiral polycyclic compounds.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28696574</pmid><doi>10.1002/anie.201706013</doi><tpages>4</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-5740-8494</orcidid><orcidid>https://orcid.org/0000-0003-2224-7234</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Alkenes Alkoxides Amides Aromatic compounds asymmetric catalysis Asymmetric synthesis Catalysts Cycloaddition divergent synthesis Enantiomers Halides Polycyclic compounds ruthenium triazenes |
| title | Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes |
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