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

Waldmann, Herbert; WEIGERDING, M; DREISBACH, C; WANDREY, C

doi:10.1002/hlca.19940770803

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons98735

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

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9C80-4

Abstract

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).