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
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
[21]  
Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3
[22]   The synthesis of homochiral ligands based on [2.2]paracyclophane [J].
Pelter, A ;
Mootoo, B ;
Maxwell, A ;
Reid, A .
TETRAHEDRON LETTERS, 2001, 42 (47) :8391-8394
[23]  
Pfaltz A., 1999, COMPREHENSIVE ASYMME, P833, DOI DOI 10.1021/CR0683515
[24]   [2.2]PHANEPHOS-ruthenium(II) complexes:: Highly active asymmetric catalysts for the hydrogenation of β-ketoesters [J].
Pye, PJ ;
Rossen, K ;
Reamer, RA ;
Volante, RP ;
Reider, PJ .
TETRAHEDRON LETTERS, 1998, 39 (25) :4441-4444
[25]   A new planar chiral bisphosphine ligand for asymmetric catalysis: Highly enantioselective hydrogenations under mild conditions [J].
Pye, PJ ;
Rossen, K ;
Reamer, RA ;
Tsou, NN ;
Volante, RP ;
Reider, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) :6207-6208
[26]  
ROSSEN K, 1997, J ORG CHEM, V62, P462
[27]   Elaboration of a novel type of planar-chiral methylene bridged biphenols based on [2.2]paracyclophanes [J].
Rozenberg, VI ;
Antonov, DY ;
Zhuravsky, RP ;
Vorontsov, EV ;
Khrustalev, VN ;
Ikonnikov, NS ;
Belokon, YN .
TETRAHEDRON-ASYMMETRY, 2000, 11 (13) :2683-2693
[28]   Asymmetric autocatalysis of a pyrimidyl alkanol induced by chiral monosubstituted [2.2]paracyclophanes [J].
Tanj, S ;
Ohno, A ;
Sato, I ;
Soai, K .
ORGANIC LETTERS, 2001, 3 (02) :287-289
[29]   Asymmetric transition metal-catalyzed allylic alkylations [J].
Trost, BM ;
VanVranken, DL .
CHEMICAL REVIEWS, 1996, 96 (01) :395-422
[30]   Designing a receptor for molecular recognition in a catalytic synthetic reaction: Allylic Alkylation [J].
Trost, BM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (08) :355-364