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Catalyst-Controlled Selective Alkylation/Cyclopropanation of Indoles with Vinyl Diazoesters.
Wang, Zhen; Xu, Guangyang; Tang, Shengbiao; Shao, Ying; Sun, Jiangtao.
Affiliation
  • Wang Z; Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , P. R. China.
  • Xu G; Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , P. R. China.
  • Tang S; Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , P. R. China.
  • Shao Y; Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , P. R. China.
  • Sun J; Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , P. R. China.
Org Lett ; 21(20): 8488-8491, 2019 Oct 18.
Article in En | MEDLINE | ID: mdl-31596104
ABSTRACT
A catalyst-controlled selective functionalization of indoles with vinyl diazoacetates has been developed. The use of gold catalysts exclusively leads to C3-alkylation products, whereas the highly diastereoselective cyclopropanation reaction is dominant for silver catalysis. Importantly, the gold and silver vinylcarbenes exhibit highly carbenic rather than vinylogous reactivity in these transformations.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2019 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2019 Document type: Article