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

doi:10.1021/acs.orglett.6b02718

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

Department of Chemistry

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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 language	English
Journal	Organic Letters
Volume	18
Issue number	23
Pages (from-to)	5990-5993
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.6b02718
Publication status	Published - 2016

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title = "Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet-Spengler-Type Reactions",

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.",

author = "Hansen, {Casper Lykke} and Ohm, {Ragnhild Gaard} and Olsen, {Lasse Bohn} and Erhad Ascic and Tanner, {David Ackland} and Nielsen, {Thomas Eiland}",

year = "2016",

doi = "10.1021/acs.orglett.6b02718",

language = "English",

volume = "18",

pages = "5990--5993",

journal = "Organic Letters",

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T1 - Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet-Spengler-Type Reactions

AU - Hansen, Casper Lykke

AU - Ohm, Ragnhild Gaard

AU - Olsen, Lasse Bohn

AU - Ascic, Erhad

AU - Tanner, David Ackland

AU - Nielsen, Thomas Eiland

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.6b02718

DO - 10.1021/acs.orglett.6b02718

M3 - Journal article

C2 - 27934390

SN - 1523-7060

VL - 18

SP - 5990

EP - 5993

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

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

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