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Gold-catalyzed oxidative cyclizations on 1,4-enynes: evidence for a γ-substituent effect on Wagner-Meerwein rearrangements.

Gold-catalyzed oxidative cyclizations of 1,4-enynes were used to study the [gamma]-effect on the Wagner-Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the [gamma]-position can direct a stereospecific 1,2-shift of the anti-[beta]-substituent regardl... Full description

Journal Title: Angewandte Chemie (International ed. in English) April 8, 2013, Vol.52(15), pp.4229-4234
Main Author: Ghorpade, Satish
Other Authors: Su, Ming-Der , Liu, Rai-Shung
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1521-3773 ; DOI: 1521-3773 ; DOI: 10.1002/anie.201210313
Link: http://search.proquest.com/docview/1324384624/?pq-origsite=primo
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title: Gold-catalyzed oxidative cyclizations on 1,4-enynes: evidence for a γ-substituent effect on Wagner-Meerwein rearrangements.
format: Article
creator:
  • Ghorpade, Satish
  • Su, Ming-Der
  • Liu, Rai-Shung
subjects:
  • Alkynes–Chemistry
  • Catalysis–Chemical Synthesis
  • Cyclization–Chemistry
  • Ketones–Chemistry
  • Molecular Structure–Chemistry
  • Organogold Compounds–Chemistry
  • Oxidation-Reduction–Chemistry
  • Stereoisomerism–Chemistry
  • Alkynes
  • Ketones
  • Organogold Compounds
ispartof: Angewandte Chemie (International ed. in English), April 8, 2013, Vol.52(15), pp.4229-4234
description: Gold-catalyzed oxidative cyclizations of 1,4-enynes were used to study the [gamma]-effect on the Wagner-Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the [gamma]-position can direct a stereospecific 1,2-shift of the anti-[beta]-substituent regardless of its intrinsic properties.
language: eng
source:
identifier: E-ISSN: 1521-3773 ; DOI: 1521-3773 ; DOI: 10.1002/anie.201210313
fulltext: fulltext
issn:
  • 15213773
  • 1521-3773
url: Link


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descriptionGold-catalyzed oxidative cyclizations of 1,4-enynes were used to study the [gamma]-effect on the Wagner-Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the [gamma]-position can direct a stereospecific 1,2-shift of the anti-[beta]-substituent regardless of its intrinsic properties.
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