The first use of chiral oxazoline ligands in the highly enantioselective diethylzinc addition to diphenylphosphinoyl imines

被引:37
作者
Zhang, XM
Lin, WQ
Gong, LZ [1 ]
Mi, AQ
Cui, X
Jiang, YZ
Choi, MCK
Chan, ASC
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China
[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
基金
中国国家自然科学基金;
关键词
diethylzinc addition; imines; oxazolines;
D O I
10.1016/S0040-4039(02)00014-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of chiral oxazolines, which had been conveniently prepared from commercially available (1S, 2S)-2-amino-1-phenylpropane-1,3-diol, was applied in the diethylzine addition to diphenylphosphinoyl imines to give high yields of 68-84% and excellent e.e values of 90-93%. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:1535 / 1537
页数:3
相关论文
共 29 条
[1]   Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].
Andersson, PG ;
Guijarro, D ;
Tanner, D .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375
[2]  
Andersson PG, 1996, SYNLETT, P727
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]  
Brandt P, 1999, CHEM-EUR J, V5, P1692, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO
[5]  
2-M
[6]   A convenient asymmetric synthesis of alpha-1-arylalkylamines through the enantioselective hydrogenation of enamides [J].
Burk, MJ ;
Wang, YM ;
Lee, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5142-5143
[7]  
Denmark S. E., 1996, J CHEM SOC CHEM COMM, P999
[8]   Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].
Enders, D ;
Reinhold, U .
TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946
[9]   Copper-amidophosphine catalyst in asymmetric addition of organozinc to imines [J].
Fujihara, H ;
Nagai, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12055-12056
[10]   Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines promoted by 2-azanorbornylmethanols [J].
Guijarro, D ;
Pinho, P ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2530-2535