Author: Chen Arh-Hwang Yen Hsiu-Hang Kuo Yu-Chen Chen Wen-Zhang
Publisher: Taylor & Francis Ltd
ISSN: 0039-7911
Source: Synthetic Communications, Vol.37, Iss.17, 2007-01, pp. : 2975-2987
Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.
Abstract
rac-2,2'-Diamino-3,3'-diethoxycarbonyl-8,8'-diphenyl-1,1'-biazulene was synthesized from diethyl 2-aminoazulene-1,3-dicarboxylate and was optically resolved into two enantiomers of S-form and R-form. The enantioselective oxidative couplings with two chiral amines [(-)-sparteine and (R)-(+)-α-methylbenzylamine] and ferric chloride catalyst, and the asymmetric couplings with two chiral oxovanadium(IV) complexes of ethyl 2-amino-4-phenylazulene-1-carboxylate, easily yielded chiral 2,2'-diamino-3,3'-diethoxycarbonyl-8,8'-diphenyl-1,1'-biazulene. Therefore, the introduction of two phenyl groups at the 8- and 8'-postions of each azulene ring using phenyl magnesium bromide via an addition-oxidation-decarboxylation mechanism resulted in 1,1'-biazulene forming a chiral C2 axis.
Related content
By Wang Lihua Li Jiding Zhao Zhiping Chen Cuixian
Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, Vol. 43, Iss. 2, 2006-02 ,pp. :
Synthesis and Characterisation of Macrocyclic Diamino Chiral Crown Ethers
By Correa Waldo H. Scott Janet L.
Molecules, Vol. 9, Iss. 6, 2004-05 ,pp. :