4.4 Article

Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 26, Pages 3706-3708

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.03.212

Keywords

Organocatalysis; Pyranone; Isomerisation; Rearrangement; Enzymatic resolution; Chiral cyclopentenone

Funding

  1. Fundacao para a Ciencia e a Tecnologia [POCI 2010]
  2. FEDER [SFRH/BD/31678/2006, POCI/QUI/56582/2004]
  3. Fundação para a Ciência e a Tecnologia [SFRH/BD/31678/2006, POCI/QUI/56582/2004] Funding Source: FCT

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A direct asymmetric synthesis of a trans-4,5-difunctionalised cyclopentenone derivative has been achieved in 55% yield and 80% ee by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO with simultaneous enzymatic resolution. (C) 2009 Elsevier Ltd. All rights reserved.

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