Highly Enantioselective Synthesis of Chiral Secondary Amines by Gold(I)/Chiral Bronsted Acid Catalyzed Tandem Intermolecular Hydroamination and Transfer Hydrogenation Reactions

被引:163
作者
Liu, Xin-Yuan
Che, Chi-Ming [1 ]
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词
TRANSITION-METAL CATALYSIS; MICROWAVE-ASSISTED CONDITIONS; PHASE-TRANSFER CATALYST; ASYMMETRIC HYDROAMINATION; COOPERATIVE CATALYSIS; ALLYLIC ALKYLATION; INTRAMOLECULAR HYDROAMINATION; REDUCTIVE AMINATION; RELAY CATALYSIS; GOLD CATALYSIS;
D O I
10.1021/ol901443b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the synthesis of enantiomerically enriched secondary amines with excellent ee values through the tandem intermolecular hydroamination/transfer hydrogenation of alkynes using a "gold(I) complex-chiral Bronsted acid" protocol is developed. The catalysis works for a wide variety of aryl, alkenyl, and aliphatic alkynes as well as anilines with different electronic properties.
引用
收藏
页码:4204 / 4207
页数:4
相关论文
共 55 条
[51]   Recent developments in enantioselective gold(I) catalysis [J].
Widenhoefer, Ross A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) :5382-5391
[52]   Gold(I)-catalyzed intra- and intermolecular hydroamination of unactivated olefins [J].
Zhang, JL ;
Yang, CG ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1798-1799
[53]   Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes [J].
Zhang, Zhibin ;
Bender, Christopher F. ;
Widenhoefer, Ross A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14148-+
[54]   Intermolecular Hydroamination of Ethylene and 1-Alkenes with Cyclic Ureas Catalyzed by Achiral and Chiral Gold(I) Complexes [J].
Zhang, Zhibin ;
Lee, Seong Du ;
Widenhoefer, Ross A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) :5372-+
[55]   Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity [J].
Zhou, Jianrong ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12220-+