Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols

被引:85
作者
Banerjee, Debasis [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
allylic alcohols; asymmetric amination; chiral phosphoric acids; palladium; phosphoramidite ligands; ASYMMETRIC ALPHA-ALLYLATION; BAYLIS-HILLMAN ADDUCTS; TERMINAL ALKYNES; BOND-CLEAVAGE; C-O; AMINES; ACTIVATION; EFFICIENT; SUBSTITUTION; ALKYLATION;
D O I
10.1002/anie.201405511
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cooperative catalysis by [Pd(dba)(2)] and the chiral phosphoric acid BA1 in combination with the phosphoramidite ligand L8 enabled the efficient enantioselective amination of racemic allylic alcohols with a variety of functionalized amines. This catalytic protocol is highly regio- and stereo-selective (up to e.r. 96: 4) and furnishes valuable chiral amines in almost quantitative yield.
引用
收藏
页码:13049 / 13053
页数:5
相关论文
共 76 条
[21]   Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353
[22]  
Grossmann A., 2012, Angew. Chem, V124, P320, DOI DOI 10.1002/ANIE.201105415
[23]   N-Heterocyclic Carbene Catalyzed Domino Reactions [J].
Grossmann, Andre ;
Enders, Dieter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) :314-325
[24]   Hydrogen- Bond- Assisted Activation of Allylic Alcohols for Palladium- Catalyzed Coupling Reactions [J].
Gumrukcu, Yasemin ;
de Bruin, Bas ;
Reek, Joost N. H. .
CHEMSUSCHEM, 2014, 7 (03) :890-896
[25]   ASYMMETRIC ALLYLIC AMINATION CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES [J].
HAYASHI, T ;
KISHI, K ;
YAMAMOTO, A ;
ITO, Y .
TETRAHEDRON LETTERS, 1990, 31 (12) :1743-1746
[26]   A general ruthenium-catalyzed synthesis of aromatic Amines [J].
Hollmann, Dirk ;
Baehn, Sebastian ;
Tillack, Annegret ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) :8291-8294
[27]   Kinetic Resolution of Indolines by Pd-Catalyzed Asymmetric Allylic Amination [J].
Hou, Xue Long ;
Zheng, Bao Hui .
ORGANIC LETTERS, 2009, 11 (08) :1789-1791
[28]  
Imm S., 2011, ANGEW CHEM, V123, P7741
[29]  
Imm S., 2010, ANGEW CHEM, V122, P8303
[30]   Improved Ruthenium-Catalyzed Amination of Alcohols with Ammonia: Synthesis of Diamines and Amino Esters [J].
Imm, Sebastian ;
Baehn, Sebastian ;
Zhang, Min ;
Neubert, Lorenz ;
Neumann, Helfried ;
Klasovsky, Florian ;
Pfeffer, Jan ;
Haas, Thomas ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7599-7603