4.4 Article

Alkoxide-catalyzed ring expansion of 1,3-cyclobutanediones with aldehydes

Journal

TETRAHEDRON LETTERS
Volume 64, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.151804

Keywords

Cyclobutanedione; Potassium ethoxide; Ring expansion; Cyclic beta-keto ester

Funding

  1. JSPS KAKENHI [JP19K05473]
  2. Kanazawa University SAKIGAKE project

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1,3-Cyclobutanediones reacted with aromatic aldehydes to produce cyclic beta-keto esters, catalyzed by a small amount of potassium ethoxide. The effects of alkoxide catalysts and spiro cyclic groups on the 1,3-cyclobutanediones were examined.
1,3-Cyclobutanediones (dialkyl ketene dimer) reacted with various aromatic aldehydes to give six-membered cyclic beta-keto esters by using a catalytic amount of potassium ethoxide. Effects of alkoxide catalysts and spiro cyclic groups at the 2,4-positions of 1,3-cyclobutanediones were investigated. (C) 2020 Published by Elsevier Ltd.

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