Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines

被引:129
作者
Akullian, LC [1 ]
Snapper, ML [1 ]
Hoveyda, AH [1 ]
机构
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
关键词
alkyl zinc reagents; asymmetric catalysis; enantioselectivity; propargylamines; zirconium;
D O I
10.1002/anie.200352081
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Readily available amino acid based chiral ligands are used in a three-component Zr-catalyzed enantioselective synthesis of propargylamines (see schemes). The reaction affords important enantiomerically enriched building blocks that are not conveniently accessible by alternative catalytic methods.
引用
收藏
页码:4244 / 4247
页数:4
相关论文
共 36 条
[31]   Catalytic asymmetric cyclocarbonylation of nitrogen-containing enynes [J].
Sturla, SJ ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5547-5550
[32]  
TRAVERSE JT, 2003, IN PRESS ORG LETT, V5
[33]   Ruthenium-catalyzed alkyne-propargyl alcohol addition.: An asymmetric total synthesis of (+)-α-kainic acid [J].
Trost, BM ;
Rudd, MT .
ORGANIC LETTERS, 2003, 5 (09) :1467-1470
[34]   Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene [J].
Wei, CM ;
Li, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5638-5639
[35]   ALIPHATIC PROPARGYLAMINES - POTENT, SELECTIVE, IRREVERSIBLE MONOAMINE OXIDASE-B INHIBITORS [J].
YU, PH ;
DAVIS, BA ;
BOULTON, AA .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (20) :3705-3713
[36]   Evaluation of chiral oxazolines for the highly enantioselective diethylzinc addition to N-(diphenylphosphinoyl) imines [J].
Zhang, XM ;
Zhang, HL ;
Lin, WQ ;
Gong, LZ ;
Mi, AQ ;
Cui, X ;
Jiang, YZ ;
Yu, KB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4322-4329