Gold(I)-Catalyzed enantioselective synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloadditions of 3/2-substituted 2/3-vinylindoles
Articolo
Data di Pubblicazione:
2017
Citazione:
Gold(I)-Catalyzed enantioselective synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloadditions of 3/2-substituted 2/3-vinylindoles / V. Pirovano, M. Borri, G. Abbiati, S. Rizzato, E. Rossi. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 359:11(2017 Jun 06), pp. 1912-1918. [10.1002/adsc.201700280]
Abstract:
The gold-catalyzed synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloaddition reactions of 3/2-substituted 2/3-vinylindoles with allenamides is reported. In particular, we optimized the enantioselective variant of these cycloadditions. Using allenamides as dienophiles 3-substituted 2-vinylindoles gave the corresponding carbazoles with high chemo-, regio- and enantioselectivity. Good results were obtained also with 2-methyl 3-vinylindoles even if mixtures of (Z) and (E) isomers were isolated in high er and in excellent overall yields.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
allenamides; asymmetric catalysis; [4+2] cycloadditions; gold; tetrahydrocarbazoles; vinylindoles
Elenco autori:
V. Pirovano, M. Borri, G. Abbiati, S. Rizzato, E. Rossi
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