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

Casper Lykke Hansen, Ragnhild Gaard Ohm, Lasse Bohn Olsen, Erhad Ascic, David Ackland Tanner, Thomas Eiland Nielsen

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Abstract

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.
Original languageEnglish
JournalORGANIC LETTERS
Volume18
Issue number23
Pages (from-to)5990-5993
Number of pages4
ISSN1523-7060
DOIs
Publication statusPublished - 2016

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