4.4 Article

Facile synthesis of γ-alkenylbutenolides from Baylis-Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 49, Pages 6545-6549

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.09.125

Keywords

gamma-Alkenylbutenolides; Baylis-Hillman adducts; Indium; Zinc; Barbier reaction

Funding

  1. National Research Foundation of Korea
  2. Korean Government [2011-0002570]

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Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

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