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Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst

An enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catal... Full description

Journal Title: Chemical Communications 2013, Vol.49(94), pp.11098-11100
Main Author: Shao, Qian
Other Authors: Chen, Jiean , Tu, Meihua , Piotrowski, David W. , Huang, Yong
Format: Electronic Article Electronic Article
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ID: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c3cc46757k
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recordid: rscc3cc46757k
title: Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
format: Article
creator:
  • Shao, Qian
  • Chen, Jiean
  • Tu, Meihua
  • Piotrowski, David W.
  • Huang, Yong
subjects:
  • Catalysts
  • Miscellaneous Sciences (So)
  • Components and Materials (General) (Ea)
ispartof: Chemical Communications, 2013, Vol.49(94), pp.11098-11100
description: An enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catalyst, followed by a TMSCHN 2 mediated heterocyclization. Both theoretical calculations and experimental evidence suggest the pre-organization of the transition state for the chirality determining step via a unique 7-membered intramolecular hydrogen bonding.
language:
source:
identifier: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c3cc46757k
fulltext: fulltext
issn:
  • 1359-7345
  • 1364-548X
  • 1364548X
  • 13597345
url: Link


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titleEnantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
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descriptionAn enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catalyst, followed by a TMSCHN 2 mediated heterocyclization. Both theoretical calculations and experimental evidence suggest the pre-organization of the transition state for the chirality determining step via a unique 7-membered intramolecular hydrogen bonding.
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titleEnantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
descriptionAn enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catalyst, followed by a TMSCHN 2 mediated heterocyclization. Both theoretical calculations and experimental evidence suggest the pre-organization of the transition state for the chirality determining step via a unique 7-membered intramolecular hydrogen bonding.
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titleEnantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
authorShao, Qian ; Chen, Jiean ; Tu, Meihua ; Piotrowski, David W. ; Huang, Yong
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abstractAn enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catalyst, followed by a TMSCHN 2 mediated heterocyclization. Both theoretical calculations and experimental evidence suggest the pre-organization of the transition state for the chirality determining step via a unique 7-membered intramolecular hydrogen bonding.
doi10.1039/c3cc46757k
pages11098-11100
date2013-10-31