Novel planar chiral P,N-[2.2]paracyclophane ligands:: synthesis and application in palladium-catalyzed allylic alkylation

被引：48
作者：
Wu, XW
Yuan, K
Sun, W
Zhang, MJ
Hou, XL
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Konh Joint Lab Chem Synth, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 01期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/S0957-4166(02)00790-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A series of planar chiral P,N-[2.2]paracyclophane ligands were synthesized and applied in enantio selective palladium-catalyzed allylic alkylation, in which the central chirality of [2.2]paracyclophane is the dominant stereocontrol element. The effect of the substituents attached to the phosphorus atom of these ligands on the yield and stereoselectivity of the reaction was also investigated. (C) 2003 Published by Elsevier Science Ltd.
引用
收藏
页码：107 / 112
页数：6
相关论文
共 43 条
[1]  
[Anonymous], 1993, HDB ENANTIOSELECTIVE
[2]   Asymmetric trimethylsilylcyanation of benzaldehyde catalyzed by (salen)Ti(IV) complexes derived from (R)- and/or (S)-4-hydroxy-5-formyl[2.2]paracyclophane and diamines [J].
Belokon, Y ;
Moscalenko, M ;
Ikonnikov, N ;
Yashkina, L ;
Antonov, D ;
Vorontsov, E ;
Rozenberg, V .
TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3245-3250
[3]  
Bolm C, 2000, SYNLETT, P899
[4]   A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones [J].
Burk, MJ ;
Hems, W ;
Herzberg, D ;
Malan, C ;
Zanotti-Gerosa, A .
ORGANIC LETTERS, 2000, 2 (26) :4173-4176
[5]   LIGAND ELECTRONIC EFFECTS IN ASYMMETRIC CATALYSIS - ENHANCED ENANTIOSELECTIVITY IN THE ASYMMETRIC HYDROCYANATION OF VINYLARENES [J].
CASALNUOVO, AL ;
RAJANBABU, TV ;
AYERS, TA ;
WARREN, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9869-9882
[6]   The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands [J].
Dahmen, S ;
Bräse, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5940-5941
[7]   Planar and central chiral [2.2] paracyclophane-based N,O-ligands as highly active catalysts in the diethylzinc addition to aldehydes [J].
Dahmen, S ;
Bräse, S .
CHEMICAL COMMUNICATIONS, 2002, (01) :26-27
[8]   [2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes [J].
Dahmen, S ;
Bräse, S .
ORGANIC LETTERS, 2001, 3 (25) :4119-4122
[9]   The application of ligands with planar chirality in asymmetric synthesis [J].
Dai, LX ;
Hou, XL ;
Deng, WP ;
You, SL ;
Zhou, VG .
PURE AND APPLIED CHEMISTRY, 1999, 71 (08) :1401-1405
[10]   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
12345