4.7 Article

Phosphine-promoted [3+2] cycloaddition between nonsubstituted MBH carbonates and trifluoromethyl ketones

Journal

CHINESE CHEMICAL LETTERS
Volume 26, Issue 6, Pages 646-648

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2015.03.019

Keywords

Cycloaddition; Allylic carbonate; Ylides; Trifluoromethyl ketones

Funding

  1. National Natural Science Foundation of China [21302034]
  2. Fundamental Research Funds for the Central Universities [2013HGQC0028]

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A phosphine-promoted [3 + 2] cycloaddition from readily accessible MBH (Morita-Baylis-Hillman) carbonate and aryl trifluoromethyl ketone is described. The use of methyl vinyl ketone-derived allylic carbonate rather than common acrylate-derived counterpart renders the reaction pathway exclusive for 5-endo process, which enables the expeditious preparation of a range of trifluoromethylated 2, 3-dihydrofuran in a chemospecific manner. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

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