6533b838fe1ef96bd12a48b0
RESEARCH PRODUCT
Structurally diverse second-generation [2.2]paracyclophane ketimines with planar and central chirality: syntheses, structural determination, and evaluation for asymmetric catalysis.
Frank LauterwasserMartin NiegerKalle NättinenKalle NättinenHeidi MansikkamäkiHeidi MansikkamäkiStefan Bräsesubject
chemistry.chemical_compoundPlanarChemistryStereochemistryOrganic ChemistryEnantioselective synthesisAbsolute configurationGeneral ChemistryDiethylzincChirality (chemistry)CatalysisCatalysisdescription
A set of 20 novel [2.2]paracyclophane ketimines with planar and central chirality has been synthesized from enantiomerically pure and racemic 5-acyl-4-hydroxy[2.2]paracyclophane and alpha-branched chiral amines. Their X-ray structures were determined to elucidate the three-dimensional structures and the absolute configuration. The ketimines were used as catalysts in the asymmetric 1,2-addition reactions of diethylzinc with substituted benzaldehydes to furnish chiral alcohols in up to 95 % ee.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-05-04 | Chemistry (Weinheim an der Bergstrasse, Germany) |