Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet–Spengler-Type Reactions

Hansen, Casper L.; Ohm, Ragnhild G.; Olsen, Lasse B.; Ascic, Erhad; Tanner, David; Nielsen, Thomas E.

Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet–Spengler-Type Reactions

2016

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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