Synthesis and asymmetric catalytic activity of (1 S,1′ S)-4,4′-biquinazoline-based primary amines

A series of (1 S,1′ S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were scr...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2011-02, Vol.22 (3), p.300-308
Main Authors: Cakici, Murat, Catir, Mustafa, Karabuga, Semistan, Ulukanli, Sabri, Kilic, Hamdullah
Format: Article
Language:English
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Summary:A series of (1 S,1′ S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an ( S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2011.01.009