Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design,   synthesis, application and characteristics in catalytic asymmetric   aziridination

doi:10.1016/j.tetasy.2005.09.025

CORC > 北京大学 > 化学与分子工程学院

	Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design, synthesis, application and characteristics in catalytic asymmetric aziridination
	Ma, LG ; Jiao, P ; Zhang, QH ; Xu, JX
刊名	tetrahedron asymmetry
	2005
关键词	NOZAKI-HIYAMA ALLYLATION DIELS-ALDER REACTIONS ENANTIOSELECTIVE AZIRIDINATION ALKENE AZIRIDINATION COPPER-COMPLEXES CHIRAL CATALYSTS CHELATE SIZE LIGANDS OLEFINS CYCLOPROPANATION
DOI	10.1016/j.tetasy.2005.09.025
英文摘要	A series of rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes) have been designed, synthesized, and evaluated in the catalytic asymmetric aziridination with [N-(p-toluenesulfonyl)imino]phenyliodinane (PhI=NTs) as a nitrene source. The results indicate that highly enantio selective aziridination of chalcones catalyzed by an AnBOX and CuOTf complex with up to > 99% ee and the opposite enantioselectivity, compared with the ligands of Evans et al., can be achieved. The enantio selectivity is substituent dependent with respect to chalcones. Chalcones with electron-donating substituents show higher enantio selectivities due to the stronger Lewis basicity of the oxygen of their carbonyl groups than those with electron-withdrawing substituents. The results also indicate that the coordination between the oxygen of the carbonyl group in chalcones and the ether group in alkenes with the copper in the catalyst is essential for high enantioselectivity, while the pi-pi stacking interaction between two reactants plays an importantly additional role for high enantioselectivity in asymmetric aziridination. An excellent backbone-controlled stereoselectivity was observed for the AnBOX ligands in asymmetric aziridination, as this will provide very important information for designing novel ligands. (c) 2005 Elsevier Ltd. All rights reserved.; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; SCI(E); 0; ARTICLE; 22; 3718-3734; 16
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/253706]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Ma, LG,Jiao, P,Zhang, QH,et al. Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design, synthesis, application and characteristics in catalytic asymmetric aziridination[J]. tetrahedron asymmetry,2005.
APA	Ma, LG,Jiao, P,Zhang, QH,&Xu, JX.(2005).Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design, synthesis, application and characteristics in catalytic asymmetric aziridination.tetrahedron asymmetry.
MLA	Ma, LG,et al."Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design, synthesis, application and characteristics in catalytic asymmetric aziridination".tetrahedron asymmetry (2005).