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C2-SYMMETRIC BICYCLIC DIOLS AS CHIRAL LIGANDS IN THE TITANATE-CATALYZED ENANTIOSELECTIVE ADDITION OF ALKYLZINC REAGENTS TO ALDEHYDES

MPG-Autoren
http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Zitation

Waldmann, H., WEIGERDING, M., DREISBACH, C., & WANDREY, C. (1994). C2-SYMMETRIC BICYCLIC DIOLS AS CHIRAL LIGANDS IN THE TITANATE-CATALYZED ENANTIOSELECTIVE ADDITION OF ALKYLZINC REAGENTS TO ALDEHYDES. HELVETICA CHIMICA ACTA, 77(8), 2111-2116. doi:10.1002/hlca.19940770803.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-0014-9C80-4
Zusammenfassung
Enantiomerically pure C-2-symmetric 1,4-diols embodying bicyclic C-frameworks were synthesized by means of asymmetric carbo-Diels-Alder reactions as key steps (Scheme 1). They were investigated as chiral ligands in the enantioselective addition of ZnEt(2) to aromatic aldehydes. In the presence of 20-40 mol-% of the titanates formed from these diols and [Ti(i-PrO)(4)] at -78 degrees, the respective 1-arylpropanols were obtained with enantiomer ratios up to 93:7(Scheme 2, Table).