Synthesis of novel N,O-planar chiral [2,2]paracyclophane ligands and their application as catalysts in the addition of diethylzinc to aldehydes

被引:52
作者
Wu, XW
Hou, XL
Dai, LX
Tao, J
Cao, BX
Sun, J
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 Kong 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(01)00102-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of novel planar chiral N,O-[2,2]paracyclophane ligands were synthesised and applied as catalysts in the enantioselective addition of diethylzinc to aldehydes. The results indicate that the planar chirality of [2,2]paracyclophane, not the central chirality of the oxazoline, is the dominant stereocontrolling element. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:529 / 532
页数:4
相关论文
共 34 条
[11]  
Fringuelli F, 2000, CHEM LETT, P38
[12]  
Hayashi T., 1995, FERROCENES
[13]   Novel N,S- and N,Se-planar chiral [2,2]paracyclophane ligands:: synthesis and application in Pd-catalyzed allylic alkylation [J].
Hou, XL ;
Wu, XW ;
Dai, LX ;
Cao, BX ;
Sun, J .
CHEMICAL COMMUNICATIONS, 2000, (13) :1195-1196
[14]   Oxazoline mediated routes to a unique amino-acid, 4-amino-13-carboxy[2.2]paracyclophane, of planar chirality [J].
Marchand, A ;
Maxwell, A ;
Mootoo, B ;
Pelter, A ;
Reid, A .
TETRAHEDRON, 2000, 56 (37) :7331-7338
[15]  
Muñiz K, 2000, CHEM-EUR J, V6, P2309, DOI 10.1002/1521-3765(20000703)6:13<2309::AID-CHEM2309>3.0.CO
[16]  
2-N
[17]   [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
[18]   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
[19]   ASYMMETRIC INDUCTION IN THE OXIDATION OF [2.2]PARACYCLOPHANE-SUBSTITUTED SELENIDES - APPLICATION OF CHIRALITY TRANSFER IN THE SELENOXIDE [2,3] SIGMATROPIC REARRANGEMENT [J].
REICH, HJ ;
YELM, KE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5672-5679
[20]   MACRO RINGS .35. TRANSANNULAR DIRECTIVE INFLUENCES IN ELECTROPHILIC SUBSTITUTION OF MONOSUBSTITUTED [2.2]PARACYCLOPHANES [J].
REICH, HJ ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (13) :3505-&