Enamine protonation: A chiral diamine catalyzes an asymmetric Friedel–Crafts reaction through catalytic enantioselective protonation of an enamine. This process can be applied to a range of α-substituted acroleins and indoles with high yields of products and high enantioselectivity (up to 94 % ee). An OH/π interaction between H2O and the indole ring was found to play an important role in the transition state (see scheme).
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Fu et al. (2011) studied this question.
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