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

ÇAKICI, Murat; Catir, MUSTAFA; Karabuga, Semistan; Ulukanli, Sabri; KILIÇ, Hamdullah

doi:10.1016/j.tetasy.2011.01.009

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

ÇAKICI M., Catir M., Karabuga S., Ulukanli S., KILIÇ H.

TETRAHEDRON-ASYMMETRY, cilt.22, sa.3, ss.300-308, 2011 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 22 Sayı: 3
Basım Tarihi: 2011
Doi Numarası: 10.1016/j.tetasy.2011.01.009
Dergi Adı: TETRAHEDRON-ASYMMETRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.300-308
Erzincan Binali Yıldırım Üniversitesi Adresli: Evet

Özet

A series of (1S,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%. (C) 2011 Elsevier Ltd. All rights reserved.