Enantioselective addition of organolithium reagents on isoquinoline

被引:52
作者
Alexakis, A [1 ]
Amiot, F [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1016/S0957-4166(02)00531-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1-methyl-1,2-dihydroisoquinoline and 1-butyl-1,2-dihydroisoquinoline were obtained by enantio selective addition of organolithium reagents on the isoquinoline. (-)-Sparteine was used as an external catalytic chiral ligand and an enantiomeric excess of 57% could be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2117 / 2122
页数:6
相关论文
共 14 条
[1]  
AMBRAMOVITCH RA, 1967, CHEM COMMUN, P274
[2]   An enantioselective access to 1-alkyl-1,2-dihydroisoquinolines and 1-alkyl-, 3-alkyl-, and 1,3-dialkyl-1,2,3,4-tetrahydroisoquinolines [J].
Barbier, D ;
Marazano, C ;
Riche, C ;
Das, BC ;
Potier, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1767-1772
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]  
Boulton A.J., 1984, Comprehensive Heterocyclic Chemistry: The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds, V2
[5]   Enantioselective addition of organolithium reagents to 3,4-dihydroisoquinoline in the presence of (-)-sparteine as an external ligand. Application for the synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Sokolowska, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (10) :1435-1440
[6]  
COMINS DL, 1991, HETEROCYCLES, V32, P1869
[7]   ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].
DENMARK, SE ;
NAKAJIMA, N ;
NICAISE, OJC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798
[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]  
FRAENKEL G, 1968, TETRAHEDRON LETT, V8, P1825
[10]  
GIAM CS, 1971, TETRAHEDRON LETT, V12, P4961