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Enantioselective Synthesis of beta -Pyrazole-Substituted Alcohols through an Asymmetric Ring-Opening Reaction of meso-Epoxides

An efficient and practical synthesis of optically pure beta -pyrazole-substituted alcohols was achieved by an asymmetric ring-opening reaction of meso-epoxides with pyrazole derivatives as the nucleophile. In the presence of 1mol% of an N,N'-dioxide-Sc(OTf) sub(3) complex, excellent enantioselectivi... Full description

Journal Title: Chemistry: A European Journal March 2012, Vol.18(12), pp.3473-3477
Main Author: Hu, Xiaolei
Other Authors: Gao, Bo , Chu, Yangyang , Li, Wei , Liu, Xiaohua , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201103792
Link: http://search.proquest.com/docview/1800490091/?pq-origsite=primo
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title: Enantioselective Synthesis of beta -Pyrazole-Substituted Alcohols through an Asymmetric Ring-Opening Reaction of meso-Epoxides
format: Article
creator:
  • Hu, Xiaolei
  • Gao, Bo
  • Chu, Yangyang
  • Li, Wei
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Synthesis (Chemistry)
  • Nucleophiles
  • Derivatives
  • Alcohols
  • Asymmetry
  • Pyrazole
  • Oxides
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, March 2012, Vol.18(12), pp.3473-3477
description: An efficient and practical synthesis of optically pure beta -pyrazole-substituted alcohols was achieved by an asymmetric ring-opening reaction of meso-epoxides with pyrazole derivatives as the nucleophile. In the presence of 1mol% of an N,N'-dioxide-Sc(OTf) sub(3) complex, excellent enantioselectivity and yields were obtained from meso-epoxides. The process could also be used for a mixture of cis- and trans-stilbene oxides. A proposed transition-state model is provided.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201103792
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleEnantioselective Synthesis of beta -Pyrazole-Substituted Alcohols through an Asymmetric Ring-Opening Reaction of meso-Epoxides
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subjectSynthesis (Chemistry) ; Nucleophiles ; Derivatives ; Alcohols ; Asymmetry ; Pyrazole ; Oxides ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionAn efficient and practical synthesis of optically pure beta -pyrazole-substituted alcohols was achieved by an asymmetric ring-opening reaction of meso-epoxides with pyrazole derivatives as the nucleophile. In the presence of 1mol% of an N,N'-dioxide-Sc(OTf) sub(3) complex, excellent enantioselectivity and yields were obtained from meso-epoxides. The process could also be used for a mixture of cis- and trans-stilbene oxides. A proposed transition-state model is provided.
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descriptionAn efficient and practical synthesis of optically pure beta -pyrazole-substituted alcohols was achieved by an asymmetric ring-opening reaction of meso-epoxides with pyrazole derivatives as the nucleophile. In the presence of 1mol% of an N,N'-dioxide-Sc(OTf) sub(3) complex, excellent enantioselectivity and yields were obtained from meso-epoxides. The process could also be used for a mixture of cis- and trans-stilbene oxides. A proposed transition-state model is provided.
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abstractAn efficient and practical synthesis of optically pure beta -pyrazole-substituted alcohols was achieved by an asymmetric ring-opening reaction of meso-epoxides with pyrazole derivatives as the nucleophile. In the presence of 1mol% of an N,N'-dioxide-Sc(OTf) sub(3) complex, excellent enantioselectivity and yields were obtained from meso-epoxides. The process could also be used for a mixture of cis- and trans-stilbene oxides. A proposed transition-state model is provided.
doi10.1002/chem.201103792
urlhttp://search.proquest.com/docview/1800490091/
date2012-03-19