Ru-catalyzed asymmetric hydrogenation of α-phthalimide ketones and 1,3-diaryl diketones using 4,4′-substituted BINAPs

被引:34
作者
Hu, AG [1 ]
Lin, WB [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ol0474812
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A family of tunable precatalysts [NH2Et2][{Ru(4,4'-BINAP)Cl}(2)(mu-Cl)(3)] was synthesized and used for highly enantioselective hydrogenation of phthalimide-protected amino ketones and 1,3-diaryldiketones. The bulky groups on the 4,4'-positions of BINAP were believed to be responsible for the enhancement of enantioselectivity (and diasteroselectivity) in these reactions.
引用
收藏
页码:455 / 458
页数:4
相关论文
共 35 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   OXIDATION OF N-AMINOQUINAZOLONES IN THE PRESENCE OF ALKENES - EVIDENCE AGAINST INVOLVEMENT OF N-NITRENES [J].
ATKINSON, RS ;
KELLY, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1362-1363
[3]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[4]   Highly enantioselective ruthenium-catalyzed reduction of ketones employing readily available peptide ligands [J].
Bogevig, A ;
Pastor, IM ;
Adolfsson, H .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (01) :294-302
[5]   Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide [J].
Brown, RA ;
Pollet, P ;
McKoon, E ;
Eckert, CA ;
Liotta, CL ;
Jessop, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1254-1255
[6]   Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].
Cardillo, G ;
Tomasini, C .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&
[7]   Multiple dendritic catalysts for asymmetric transfer hydrogenation [J].
Chen, YC ;
Wu, TF ;
Deng, JG ;
Liu, H ;
Cui, X ;
Zhu, J ;
Jiang, YZ ;
Choi, MCK ;
Chan, ASC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5301-5306
[8]   Ruthenium-catalyzed asymmetric reduction of 1,3-diketones using transfer hydrogenation [J].
Cossy, J ;
Eustache, F ;
Dalko, PI .
TETRAHEDRON LETTERS, 2001, 42 (30) :5005-5007
[9]   A novel system consisting of easily recyclable dendritic Ru-BINAP catalyst for asymmetric hydrogenation [J].
Deng, GJ ;
Fan, QH ;
Chen, XM ;
Liu, DS ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2002, (15) :1570-1571
[10]   The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].
Dorta, R ;
Egli, P ;
Zurcher, F ;
Togni, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858