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Chiral N,N'-Dioxide-Scandi um(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles

The first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asym... Full description

Journal Title: Chemistry: A European Journal December 2016, Vol.22(50), pp.18254-18258
Main Author: Zheng, Jianfeng
Other Authors: Lin, Lili , Dai, Li , Yuan, Xiao , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201604088
Link: http://search.proquest.com/docview/1864568341/?pq-origsite=primo
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title: Chiral N,N'-Dioxide-Scandi um(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles
format: Article
creator:
  • Zheng, Jianfeng
  • Lin, Lili
  • Dai, Li
  • Yuan, Xiao
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Activation
  • Indoles
  • Formations
  • Alcohols
  • Chemical Reactions
  • Asymmetry
  • Lewis Acid
  • Alkylation
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, December 2016, Vol.22(50), pp.18254-18258
description: The first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry of the reaction. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee. A range of functional groups were also tolerated under the mild reaction conditions. Moreover, this strategy gives concise access to enantioenriched indole-fused benzoxocines. Chiral catalysis: The first chiral Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted N-protected indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201604088
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleChiral N,N'-Dioxide-Scandi um(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles
creatorZheng, Jianfeng ; Lin, Lili ; Dai, Li ; Yuan, Xiao ; Liu, Xiaohua ; Feng, Xiaoming
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ispartofChemistry: A European Journal, December 2016, Vol.22(50), pp.18254-18258
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subjectActivation ; Indoles ; Formations ; Alcohols ; Chemical Reactions ; Asymmetry ; Lewis Acid ; Alkylation ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionThe first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry of the reaction. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee. A range of functional groups were also tolerated under the mild reaction conditions. Moreover, this strategy gives concise access to enantioenriched indole-fused benzoxocines. Chiral catalysis: The first chiral Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted N-protected indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee.
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titleChiral N,N'-Dioxide-Scandi um(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles
descriptionThe first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry of the reaction. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee. A range of functional groups were also tolerated under the mild reaction conditions. Moreover, this strategy gives concise access to enantioenriched indole-fused benzoxocines. Chiral catalysis: The first chiral Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted N-protected indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee.
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titleChiral N,N'-Dioxide-Scandi um(III) Complex-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of ortho-Hydroxybenzyl Alcohols with C3-Substituted N-Protected Indoles
authorZheng, Jianfeng ; Lin, Lili ; Dai, Li ; Yuan, Xiao ; Liu, Xiaohua ; Feng, Xiaoming
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abstractThe first Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry of the reaction. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee. A range of functional groups were also tolerated under the mild reaction conditions. Moreover, this strategy gives concise access to enantioenriched indole-fused benzoxocines. Chiral catalysis: The first chiral Lewis acid catalyzed asymmetric Friedel-Crafts alkylation reaction of ortho-hydroxybenzyl alcohols with C3-substituted N-protected indoles is described. A chiral N,N'-dioxide Sc(OTf) sub(3) complex served not only to promote formation of ortho-quinone methides (o-QMs) in situ but also induced the asymmetry. This methodology enables a novel activation of ortho-hydroxybenzyl alcohols, thus affording the desired chiral diarylindol-2-ylmethanes in up to 99% yield and 99% ee.
doi10.1002/chem.201604088
urlhttp://search.proquest.com/docview/1864568341/
date2016-12-12