Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde

Authors
Baskaran, S Aurich, HG Biesemeier, F Harms, K
Citation
S. Baskaran et al., Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde, J CHEM S P1, (22), 1998, pp. 3717-3724
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
22
Year of publication
1998
Pages
3717 - 3724
Database
ISI
SICI code
0300-922X(19981121):22<3717:CFHFNA>2.0.ZU;2-6
Abstract
Highly diastereoselective intramolecular cycloaddition of nitrones 5-7 and 16, as well as oximes 11-13 that are easily accessible from diethyl (R,R)-t artrate, affords bicyclic compounds 8-10 and 17. The tetracyclic compound 1 4 is formed as the main product by an intramolecular domino reaction of dio xime 11. Some of the bicyclic compounds and the tetracyclic compound 14 are tested as chiral ligands in the enantioselective addition of diethylzinc t o benzaldehyde. An ee of 93% was achieved in the presence of the best ligan d.