A titanium-catalyzed three-component coupling to generate α,β-unsaturated β-iminoamines

被引:123
作者
Cao, CS [1 ]
Shi, YH [1 ]
Odom, AL [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
D O I
10.1021/ja0284714
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The three-component coupling of an amine, alkyne, and isonitrile is facilitated by a titanium complex bearing the N,N-di(pyrrolyl-α-methyl)-N-methylamine (dpma) ligand. From this methodology, α,β-unsaturated β-iminoamines are generated regioselectively with many substrates and are available on multigram scales. Copyright © 2003 American Chemical Society.
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页码:2880 / 2881
页数:2
相关论文
共 47 条
[1]   A highly reactive titanium precatalyst for intramolecular hydroamination reactions [J].
Ackermann, L ;
Bergman, RG .
ORGANIC LETTERS, 2002, 4 (09) :1475-1478
[2]   VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].
BARANGER, AM ;
WALSH, PJ ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763
[3]  
BESTCHART C, 1992, J AM CHEM SOC, V114, P5010
[4]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[5]  
2-A
[6]  
Boger D. L., 1987, HETERO DIELS ALDER M
[7]   The chemistry of β-diketiminatometal complexes [J].
Bourget-Merle, L ;
Lappert, MF ;
Severn, JR .
CHEMICAL REVIEWS, 2002, 102 (09) :3031-3065
[8]   HALOGENATED KETENES .38. CYCLOADDITION OF ALPHA,BETA-UNSATURATED IMINES WITH KETENES TO YIELD BOTH BETA-LACTAMS AND DELTA-LACTAMS [J].
BRADY, WT ;
SHIEH, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (15) :2499-2502
[9]   Hydroamination of alkynes catalyzed by a titanium pyrrolyl complex. (vol 20, pg 5012, 2001) [J].
Cao, CS ;
Ciszewski, JT ;
Odom, AL .
ORGANOMETALLICS, 2002, 21 (23) :5148-5148
[10]   Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines [J].
Cao, CS ;
Shi, YH ;
Odom, AL .
ORGANIC LETTERS, 2002, 4 (17) :2853-2856