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
[31]   Derivatives of 2-amino-2′-diphenylphosphino-1,1′-binaphthyl (MAP) and their application in asymmetric palladium(0)-catalyzed allylic substitution [J].
Vyskocil, S ;
Smrcina, M ;
Hanus, V ;
Polásek, M ;
Kocovsky, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7738-7748
[32]   The synthesis of a new generation of MAP ligands containing two types of chiral elements for asymmetric catalysis [J].
Wang, Y ;
Li, X ;
Ding, KL .
TETRAHEDRON LETTERS, 2002, 43 (01) :159-161
[33]   Synthesis of novel N,P chiral ligands for palladium-catalyzed asymmetric allylations: the effect of binaphthyl backbone an the enantioselectivity [J].
Wang, Y ;
Guo, H ;
Ding, KL .
TETRAHEDRON-ASYMMETRY, 2000, 11 (20) :4153-4162
[34]   A catalytic asymmetric Suzuki coupling for the synthesis of axially chiral biaryl compounds [J].
Yin, JJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12051-12052
[35]   Highly regio- and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands [J].
You, SL ;
Zhu, XZ ;
Luo, YM ;
Hou, XL ;
Dai, LX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7471-7472
[36]   Pd-catalyzed asymmetric allylation with a novel C2-symmetric bisphosphinite ligand:: 3R,3′R-bis(diphenylphosphinoxy)-6,6,6′,6′-tetramethyl-2S,2′S-di-4H-pyran [J].
Zhang, RZ ;
Yu, LB ;
Xu, L ;
Wang, ZQ ;
Ding, KL .
TETRAHEDRON LETTERS, 2001, 42 (43) :7659-7662