Iminophenol Ligands Derived from Chiral Regioisomeric Hydroxy[2.2]paracyclophane-carbaldehydes: the Influence of the Substitution Pattern on Asymmetric Induction
✍ Scribed by Dmitrii Yu. Antonov; Valeria I. Rozenberg; Tat'yana I. Danilova; Zoya A. Starikova; Henning Hopf
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 464 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
The planar‐chiral 12‐hydroxy[2.2]paracyclophane‐4‐carbaldehyde (3, pseudo‐FHPC) was synthesized and resolved via its Schiff bases 9 using the enantiomers of α‐phenylethylamine. The absolute configurations of the enantiomers of 3 were determined by X‐ray diffraction. Derivatives 7–21, representatives of cyclophane‐derived iminophenols with ortho, pseudo‐gem and pseudo‐ortho arrangement of the functional groups, were prepared and studied as catalysts for the enantioselective addition of diethylzinc to benzaldehyde affording the expected alcohols in up to 97 % ee. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)