Dynamic kinetic resolution of primary amines with a recyclable Pd nanocatalyst for racemization

被引:146
作者
Kim, Mahn-Joo [1 ]
Kim, Won-Hee [1 ]
Han, Kiwon [1 ]
Choi, Yoon Kyung [1 ]
Park, Jaiwook [1 ]
机构
[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea
关键词
D O I
10.1021/ol070130d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical procedure for the dynamic kinetic resolution (DKR) of primary amines has been developed. This procedure employs a palladium nanocatalyst as the racemization catalyst, a commercial lipase (Novozym-435) as the resolution catalyst, and ethyl acetate or ethyl methoxyacetate as the acyl donor. Eleven primary amines and one amino acid amide have been efficiently resolved with good yields (85-99%) and high enantiomeric excesses (97-99%).
引用
收藏
页码:1157 / 1159
页数:3
相关论文
共 22 条
[1]  
Alexeeva M, 2002, ANGEW CHEM INT EDIT, V41, P3177, DOI 10.1002/1521-3773(20020902)41:17<3177::AID-ANIE3177>3.0.CO
[2]  
2-P
[3]   Dynamic kinetic resolution of amino acid amide catalyzed by D-aminopeptidase and α-amino-ε-caprolactam racemase [J].
Asano, Y ;
Yamaguchi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7696-7697
[4]   Directed evolution of an amine oxidase for the preparative deracemisation of cyclic secondary amines [J].
Carr, R ;
Alexeeva, M ;
Dawson, MJ ;
Gotor-Fernández, V ;
Humphrey, CE ;
Turner, NJ .
CHEMBIOCHEM, 2005, 6 (04) :637-639
[5]   Aminocyclopentadienyl ruthenium complexes as racemization catalysts for dynamic kinetic resolution of secondary alcohols at ambient temperature [J].
Choi, JH ;
Choi, YK ;
Kim, YH ;
Park, ES ;
Kim, EJ ;
Kim, MJ ;
Park, JW .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1972-1977
[6]  
Choi JH, 2002, ANGEW CHEM INT EDIT, V41, P2373, DOI 10.1002/1521-3773(20020703)41:13<2373::AID-ANIE2373>3.0.CO
[7]  
2-7
[8]   Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines [J].
Choi, YK ;
Kim, MJ ;
Ahn, Y ;
Kim, MJ .
ORGANIC LETTERS, 2001, 3 (25) :4099-4101
[9]   A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines [J].
Dunsmore, CJ ;
Carr, R ;
Fleming, T ;
Turner, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2224-2225
[10]   Dynamic kinetic resolution of secondary alcohols by enzyme-metal combinations in ionic liquid [J].
Kim, MJ ;
Kim, HM ;
Kim, D ;
Ahn, Y ;
Park, J .
GREEN CHEMISTRY, 2004, 6 (09) :471-474