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A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.

Chiral rings made easy: Chiral azetidin‐3‐ones have been easily prepared from chiral N‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection step... Full description

Journal Title: Angewandte Chemie (International ed. in English) March 28, 2011, Vol.50(14), pp.3236-3239
Main Author: Ye, Longwu
Other Authors: He, Weimin , Zhang, Liming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201007624
Link: http://search.proquest.com/docview/858776061/?pq-origsite=primo
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title: A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.
format: Article
creator:
  • Ye, Longwu
  • He, Weimin
  • Zhang, Liming
subjects:
  • Alkynes–Chemistry
  • Azetidines–Chemical Synthesis
  • Catalysis–Chemistry
  • Gold–Chemistry
  • Molecular Structure–Chemistry
  • Oxidation-Reduction–Chemistry
  • Stereoisomerism–Chemistry
  • Alkynes
  • Azetidines
  • Gold
ispartof: Angewandte Chemie (International ed. in English), March 28, 2011, Vol.50(14), pp.3236-3239
description: Chiral rings made easy: Chiral azetidin‐3‐ones have been easily prepared from chiral N‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection steps, and allows its removal from the azetidine ring under acidic conditions.
language: eng
source:
identifier: E-ISSN: 1521-3773 ; DOI: 10.1002/anie.201007624
fulltext: fulltext
issn:
  • 15213773
  • 1521-3773
url: Link


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identifierE-ISSN: 1521-3773 ; DOI: 10.1002/anie.201007624
subjectAlkynes–Chemistry ; Azetidines–Chemical Synthesis ; Catalysis–Chemistry ; Gold–Chemistry ; Molecular Structure–Chemistry ; Oxidation-Reduction–Chemistry ; Stereoisomerism–Chemistry ; Alkynes ; Azetidines ; Gold
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descriptionChiral rings made easy: Chiral azetidin‐3‐ones have been easily prepared from chiral N‐propargylsulfonamides, which in turn are readily accessible through chiral sulfinamide chemistry (see scheme). Using tert‐butylsulfonyl as the protecting group avoids unnecessary deprotection and reprotection steps, and allows its removal from the azetidine ring under acidic conditions.
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