4.5 Article

Platinum-Catalyzed Regioselective Formation of β-Alkoxy Ketones from Internal Alkynes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 22, Pages 4185-4188

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000484

Keywords

Platinum; Alkynes; Ketones; Regioselectivity; Cyclization

Funding

  1. National Natural Science Foundation of China [20702032, 20872098]
  2. Ministry of Education of China [IRT0846]
  3. Ministry of Science and Technology of China [2010CB833200]

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A catalytic amount of Zeise's duller and 15-crown-5 were combined to effectively promote the regioselective formation of beta-alkoxy ketones from 2-(homopropargyloxy)ethanols in dimethoxyethane The desired products were obtained in 59-98% yields with up to 17 1 exo/endo regioselectivity The methodology allows access to beta-hydroxy ketones as an aldol reaction alternative

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