Yang Li, Fernando Tur, R. Nielsen
Jan 18, 2016
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Journal
Angewandte Chemie
Abstract
The first enantioselective formal [4+2] cycloadditions of 3-nitroindoles are presented. By using 3-nitroindoles in combination with an organocatalyst, chiral dihydrocarbazole scaffolds are formed in moderate to good yields (up to 87%) and enantioselectivities (up to 97% ee). The reaction was extended to include enantioselective [4+2] cycloadditions of 3-nitrobenzothiophene. The reaction proceeds through a [4+2] cycloaddition/elimination cascade under mild reaction conditions. Furthermore, a diastereoselective reduction of an enantioenriched cycloadduct is presented. The mechanism of the reaction is discussed based on experimental and computational studies.