4.4 Article

Unexpected Beneficial Effect of ortho-Substituents on the (S)-ProlineCatalyzed Asymmetric Aldol Reaction of Acetone with Aromatic Aldehydes

Journal

SYNLETT
Volume 25, Issue 7, Pages 961-964

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340920

Keywords

aldehyde; aldol reaction; asymmetric catalysis; organocatalysis; proline

Funding

  1. Max Planck Society
  2. HPLC department

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An intriguing effect of electronegative 2,6-substituents on the stereochemical outcome of (S)-proline-catalyzed aldol reactions between benzaldehyde derivatives and acetone is reported. Remarkably high enantioselectivities can be achieved with such substrates.

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