Axially dissymmetric binaphthyldiimine chiral salen-type ligands for copper-catalyzed asymmetric aziridination

Axially dissymmetric chiral salen-type ligands 1– 4 and 7 were prepared from the reaction of ( R)-(+)-1,1′-binaphthyl-2,2′-diamine with 2,6-dichlorobenzaldehyde, 2,3-dichlorobenzaldehyde, 3,4-dichlorobenzaldehyde or salicylaldehyde in high yields, respectively. The catalytic asymmetric aziridination...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-12, Vol.12 (22), p.3105-3111
Main Authors: Shi, Min, Wang, Chuan-Jiang, Chan, Albert S.C.
Format: Article
Language:English
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Summary:Axially dissymmetric chiral salen-type ligands 1– 4 and 7 were prepared from the reaction of ( R)-(+)-1,1′-binaphthyl-2,2′-diamine with 2,6-dichlorobenzaldehyde, 2,3-dichlorobenzaldehyde, 3,4-dichlorobenzaldehyde or salicylaldehyde in high yields, respectively. The catalytic asymmetric aziridination of alkenes has been examined using these novel chiral ligands. Excellent enantioselectivity in the aziridination of cinnamates has been achieved using the C 2-symmetric chiral ligand 1. Several novel axially dissymmetric chiral salen-type ligands have been successfully synthesized and the enantioselective aziridinations catalyzed by copper have been examined using those chiral ligands.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00534-1