Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis

被引:79
作者
Wang, Y [1 ]
Li, X [1 ]
Ding, KL [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(02)00324-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This article describes the synthesis of a new type of chiral amino phosphine ligands from an amino naphthol starting material derived by asymmetric 1-aminoalkylation of 2-naphthol with (R)-1-phenylethylamine and benzaldehyde. The asymmetric induction properties of the ligands in the Pd(0)-catalyzed allylic substitution of 1,3-diphenylprop-2-en-1-yl acetate with dimethyl malonate has also been investigated, with near-quantitative yields and ee of up to 72.2% of the product being obtained under the optimized reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1291 / 1297
页数:7
相关论文
共 36 条
[1]  
[Anonymous], ANGEW CHEM INT ED EN
[2]  
[Anonymous], COMPREHENSIVE ASYMME
[3]   Catalytic asymmetric vinylation of ketone enolates [J].
Chieffi, A ;
Kamikawa, K ;
Åhman, J ;
Fox, JM ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (12) :1897-1900
[4]   Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation [J].
Cimarelli, C ;
Mazzanti, A ;
Palmieri, G ;
Volpini, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4759-4765
[5]   ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].
DAWSON, GJ ;
FROST, CG ;
WILLIAMS, JMJ .
TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150
[6]   Importance of planar chirality in chiral catalysts with three chiral elements:: The role of planar chirality in 2′-substituted 1,1′-P,N-Ferrocene ligands on the enantioselectivity in Pd-catalyzed allylic substitution [J].
Deng, WP ;
You, SL ;
Hou, XL ;
Dai, LX ;
Yu, YH ;
Xia, W ;
Sun, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6508-6519
[7]   On the role of planar chirality:: a tunable enantioselectivity in palladium-catalyzed allylic alkylation with planar chiral 1,1′-P,N-ferrocene ligands [J].
Deng, WP ;
Hou, XL ;
Dai, LX ;
Yu, YH ;
Xia, W .
CHEMICAL COMMUNICATIONS, 2000, (04) :285-286
[8]  
Ding KL, 1999, CHEM-EUR J, V5, P1734, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1734::AID-CHEM1734>3.3.CO
[9]  
2-7
[10]   Proline-based P, N ligands in asymmetric allylation and the Heck reaction [J].
Gilbertson, SR ;
Xie, DJ ;
Fu, ZC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7240-7246