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Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity.
Chen, Ching-Nung; Cheng, Wei-Min; Wang, Jian-Kai; Chao, Tzu-Hsuan; Cheng, Mu-Jeng; Liu, Rai-Shung.
Afiliación
  • Chen CN; Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
  • Cheng WM; Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
  • Wang JK; Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
  • Chao TH; Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC.
  • Cheng MJ; Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC.
  • Liu RS; Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
Angew Chem Int Ed Engl ; 60(9): 4479-4484, 2021 02 23.
Article en En | MEDLINE | ID: mdl-33230944
This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2021 Tipo del documento: Article Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2021 Tipo del documento: Article Pais de publicación: Alemania