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.
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]
Gold(I)-Catalyzed enantioselective synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloadditions of 3/2-substituted 2/3-vinylindoles
V. Pirovano
Primo
;G. Abbiati;S. RizzatoPenultimo
;E. Rossi
Ultimo
2017
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.File | Dimensione | Formato | |
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