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Solvent‐Dependent Enantiodivergent Friedel‐Crafts Reaction of Arylsulfonyl Indoles with 1‐Naphthols
Author(s) -
Chang ChiaHao,
Sathishkumar Nadaraj,
Liao YuTing,
Chen HsinTsung,
Han JengLiang
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901360
Subject(s) - chemistry , bifunctional , cinchona , friedel–crafts reaction , toluene , enantiomer , organic chemistry , imine , solvent , cinchona alkaloids , isomerization , medicinal chemistry , catalysis , enantioselective synthesis
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.