4.4 Article

Organocatalytic annulation of aldehydes and o-quinone methides: A facile access to dihydrocoumarins

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 50, Pages 5649-5652

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.11.006

Keywords

Organocatalysis; o-Quinone methide; Dihydrocoumarin

Funding

  1. Thousand Plan Youth Program
  2. Fundamental Research Funds for the Central Universities
  3. East China University of Science Technology

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A [4+2] annulation of aldehydes and o-quinone methides catalyzed by a secondary amine is developed. This process leads to biologically important dihydrocoumarins in moderate to good yields after oxidation. In addition, the employment of a chiral secondary amine catalyst allows access to optically active dihydrocoumarins with up to 64% ee. (C) 2016 Elsevier Ltd. All rights reserved.

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