Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 21, Pages 6179-6195Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601893
Keywords
pi-pi stacking; amines; asymmetric synthesis; diastereoselectivity; arylimines; carbanions
Categories
Ask authors/readers for more resources
N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at C1 depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by pi-pi stacking interactions with the ring joined to the carbanionic centre. The stercoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl)arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available