Multicomponent one-pot procedure for the synthesis of free α-chiral amines from aldehydes

被引:45
作者
Côté, A [1 ]
Charette, AB [1 ]
机构
[1] Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
关键词
D O I
10.1021/jo0516483
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of free a-chiral amines by a one-pot multicomponent procedure from commercially available starting materials is described. This enantioselective reaction involves a catalytic asymmetric addition of dialkylzinc reagents to N-diphenylphosphinoylimines with use of an air-stable precatalyst complex 1. The a-chiral amines are prepared with a one-pot procedure from alkyl and aryl aldehydes in good yield (41-90%) and with excellent enantioselectivity (90-97% ee).
引用
收藏
页码:10864 / 10867
页数:4
相关论文
共 53 条
[1]   Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].
Akullian, LC ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247
[2]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[3]   Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand [J].
Boezio, AA ;
Pytkowicz, J ;
Côté, A ;
Charette, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14260-14261
[4]   Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines [J].
Boezio, AA ;
Charette, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1692-1693
[5]   One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketimines [J].
Borg, G ;
Cogan, DA ;
Ellman, JA .
TETRAHEDRON LETTERS, 1999, 40 (37) :6709-6712
[6]  
Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P2294, DOI 10.1002/1521-3773(20000703)39:13<2294::AID-ANIE2294>3.0.CO
[7]  
2-J
[8]  
Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P4414, DOI 10.1002/1521-3773(20001215)39:24<4414::AID-ANIE4414>3.0.CO
[9]  
2-C
[10]   New methods in combinatorial chemistry - robotics and parallel synthesis [J].
Cargill, JF ;
Lebl, M .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1997, 1 (01) :67-71