Solvent‐Dependent Enantiodivergent Friedel‐Crafts Reaction of Arylsulfonyl Indoles with 1‐Naphthols

Solvent‐Dependent Enantiodivergent Friedel‐Crafts Reaction of Arylsulfonyl Indoles with 1‐Naphthols

We reported a solvent‐controlled enantiodivergent Friedel‐Crafts reaction of 1‐naphthols with vinylogous imine intermediates, which were generated from arylsulfonyl indoles. This reaction was catalyzed by a single cinchona alkaloid bifunctional organocatalyst and could produce both enantiomers by us...

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Veröffentlicht in:Advanced synthesis & catalysis 2020-02, Vol.362 (4), p.903-912
Hauptverfasser: Chang, Chia‐Hao, Sathishkumar, Nadaraj, Liao, Yu‐Ting, Chen, Hsin‐Tsung, Han, Jeng‐Liang
Format: Artikel
Sprache:eng
Schlagworte:
1-Naphthols
Enantiodivergent
Enantiomers
Enthalpy
Friedel-Crafts
Friedel-Crafts reaction
Indoles
Organocatalysis
Solvents
Toluene
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container_end_page 912
container_issue 4
container_start_page 903
container_title Advanced synthesis & catalysis
container_volume 362
creator Chang, Chia‐Hao
Sathishkumar, Nadaraj
Liao, Yu‐Ting
Chen, Hsin‐Tsung
Han, Jeng‐Liang
description We reported a solvent‐controlled enantiodivergent Friedel‐Crafts reaction of 1‐naphthols with vinylogous imine intermediates, which were generated from arylsulfonyl indoles. This reaction was catalyzed by a single cinchona alkaloid bifunctional organocatalyst and could produce both enantiomers by using toluene or 1,2‐DCE as the solvents. Eyring plot analysis revealed that enthalpy‐entropy compensation dominates this enantiodivergent reaction. DFT calculation was used to probe and compare the R‐ and S‐selective pathways.
doi_str_mv 10.1002/adsc.201901360
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subjects 1-Naphthols
Enantiodivergent
Enantiomers
Enthalpy
Friedel-Crafts
Friedel-Crafts reaction
Indoles
Organocatalysis
Solvents
Toluene
title Solvent‐Dependent Enantiodivergent Friedel‐Crafts Reaction of Arylsulfonyl Indoles with 1‐Naphthols
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