Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet–Spengler-Type Reactions
2016
Hansen, Casper L. | Ohm, Ragnhild G. | Olsen, Lasse B. | Ascic, Erhad | Tanner, David | Nielsen, Thomas E.
A synthetic strategy for the synthesis of chiral tetrahydrocarbazoles (THCAs) has been developed. The strategy relies on two types of 6-exo-trig cyclization of 3-substituted indole substrates. Enantioselective domino Friedel–Crafts-type reactions leading to THCAs can be catalyzed by chiral phosphoric acid derivatives (with up to >99% ee), and the first examples of exocyclic Pictet–Spengler reactions to form THCAs are reported.
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