BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis

被引:61
作者
Gladiali, Serafino [1 ]
Alberico, Elisabetta [2 ]
Junge, Kathrin [3 ]
Beller, Matthias [3 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[2] CNR, Ist Chim Biomol, I-07040 Maplewood, Italy
[3] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; P-DONOR LIGANDS; PHOSPHORUS LIGANDS; ACID-DERIVATIVES; 3+2 ANNULATIONS; PHOSPHINES; CHEMISTRY; ESTERS; IMINES; CYCLOADDITION;
D O I
10.1039/c0cs00164c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The atropisomeric structure of 4,5-dihydro-3H-dinaphtho[2,1-c; 1',2'-e] phosphepine is the common axially chiral scaffold of a library of monophosphine ligands nicknamed BINEPINES that have shown a quite remarkable stereoselection efficiency in a broad variety of enantioselective reactions involving the formation of new C-H or C-C or C-X bonds. In this critical review the properties and scope of this type of chiral ligands are illustrated (70 references).
引用
收藏
页码:3744 / 3763
页数:20
相关论文
共 75 条
[1]   Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis:: Hydrogen-transfer reduction of α,β-unsaturated acid derivatives by rhodiuni/Ph-binepine catalysts [J].
Alberico, Elisabetta ;
Nieddu, Ilenia ;
Taras, Rossana ;
Gladiali, Serafino .
HELVETICA CHIMICA ACTA, 2006, 89 (08) :1716-1729
[2]   Dimethoxydibenzophosphepine: An Axially Chiral Monophosphane for Efficient Asymmetric Catalysis [J].
Alberico, Elisabetta ;
Karandikar, Satyajit ;
Gladiali, Serafino .
CHEMCATCHEM, 2010, 2 (11) :1395-1398
[3]   Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis. Asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters by Pd/BINEPINE catalysts [J].
Alberico, Elisabetta ;
Gladiali, Serafino ;
Taras, Rossana ;
Junge, Kathrin ;
Beller, Matthias .
TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) :1406-1410
[4]  
ALEXAKIS A, COMMUNICATION
[5]   THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II) [J].
ALLEN, DW ;
TAYLOR, BF .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01) :51-54
[6]   Enantioselective nucleophilic catalysis:: The synthesis of aza-β-lactams through [2+2] cycloadditions of ketenes with azo compounds [J].
Berlin, Jacob M. ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) :7048-7050
[7]   Dabbling with air-stable organoaluminum species [J].
Biswas, K ;
Chapron, A ;
Cooper, T ;
Fraser, PK ;
Novak, A ;
Prieto, O ;
Woodward, S .
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :511-518
[8]   PH-functional phosphines with 1,1′-biphenyl-2,2′-bis(methylene) and 1,1′-binaphthyl-2,2′-bis(methylene) backbones [J].
Bitterer, F ;
Herd, O ;
Kühnel, M ;
Stelzer, O ;
Weferling, N ;
Sheldrick, WS ;
Hahn, J ;
Nagel, S ;
Rösch, N .
INORGANIC CHEMISTRY, 1998, 37 (25) :6408-6417
[9]   Platinum(II) Catalysts for Highly Enantioselective 1,6-Enyne Cycloisomerizations. Synthetic, Structural, and Catalytic Studies [J].
Brissy, Delphine ;
Skander, Myriem ;
Jullien, Helene ;
Retailleau, Pascal ;
Marinetti, Angela .
ORGANIC LETTERS, 2009, 11 (10) :2137-2139
[10]  
Cai DW, 1999, ORG SYNTH, V76, P6