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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Published inAdvanced synthesis & catalysis Vol. 362; no. 4; pp. 903 - 912
Main Authors Chang, Chia‐Hao, Sathishkumar, Nadaraj, Liao, Yu‐Ting, Chen, Hsin‐Tsung, Han, Jeng‐Liang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.02.2020
Wiley Subscription Services, Inc
Subjects
1-Naphthols
Chemistry
Chemistry, Applied
Chemistry, Organic
Enantiodivergent
Enantiomers
Enthalpy
Friedel-Crafts
Friedel-Crafts reaction
Indoles
Organocatalysis
Physical Sciences
Science & Technology
Solvents
Toluene
ALDOL
3-INDOLYLMETHANOLS
ALPHA-SELENENYLATION
Enantiodivergent
CATALYST
Organocatalysis
DIASTEREO
MICHAEL ADDITION
Friedel-Crafts
NITROALKANES
ENANTIOSELECTIVE ORGANOCATALYTIC CONSTRUCTION
SWITCH
1-Naphthols
Indoles
CYCLIZATION
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ISSN1615-4150
1615-4169
DOI10.1002/adsc.201901360

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Summary: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.
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901360