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Iminophenol Ligands Derived from Chiral Regioisomeric Hydroxy[2.2]paracyclophane‐carbaldehydes: the Influence of the Substitution Pattern on Asymmetric Induction
Author(s) -
Antonov Dmitrii Yu.,
Rozenberg Valeria I.,
Danilova Tat'yana I.,
Starikova Zoya A.,
Hopf Henning
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700823
Subject(s) - chemistry , benzaldehyde , enantiomer , diethylzinc , cyclophane , enantioselective synthesis , planar chirality , catalysis , stereochemistry , medicinal chemistry , organic chemistry , crystal structure
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)