TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s
2017
Yang, Ren-Yin | Sun, Jing | Tao, Yao | Sun, Qiu | Yan, Chao-Guo
TfOH-catalyzed one-pot sequential reaction of indoles, acetophenones (cyclic ketones), and various 3-methyleneoxindolines in toluene afforded polysubstituted tetrahydrospiro[carbazole-1,3′-indoline]s in satisfactory yields. ¹H NMR spectra and single-crystal structures indicated that the obtained tetrahydrospiro[carbazole-1,3′-indoline]s existing in an unusual trans-configuration. The reaction mechanism was believed to proceed with domino acid-catalyzed 3-alkenylation of indoles with acetophenones, Diels–Alder reaction of 3-alkyenylindoles with 3-methyleneoxindolines, and an acid-catalyzed diastereoisomerization process.
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