4.4 Article

Recyclable chiral diamine-polyoxometalate (POM) acids catalyzed asymmetric direct aldol reaction of aromatic aldehydes with long-chain aliphatic ketones

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 29, Pages 3779-3781

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.05.053

Keywords

Asymmetric organocatalysis; Aldol reaction; Long-chain aliphatic ketone; Chiral diamine; Polyoxometalate acid

Funding

  1. Natural Science Foundation of China (NSFC) [20921092]
  2. Programme Strategic Scientific Alliances between China and the Netherlands [2008DFB50130]

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In this Letter, we studied the asymmetric direct aldol reaction of long-chain aliphatic ketones with aromatic aldehydes, using chiral diamine-polyoxometalate acid combined organocatalysts. High yields (up to 90%) and enantioselectivities (up to 90% ee) were obtained under solvent-free conditions with the optimized catalyst. Furthermore, such organocatalysts could be easily recycled and reused for four times without significant loss of reactivity and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

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