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
[41]   Pd-catalyzed asymmetric allylic alkylation of glycine imino ester using a chiral phase-transfer catalyst [J].
Nakoji, M ;
Kanayama, T ;
Okino, T ;
Takemoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7418-7423
[42]   Chiral phosphine-free Pd-mediated asymmetric allylation of prochiral enolate with a chiral phase-transfer catalyst [J].
Nakoji, M ;
Kanayama, T ;
Okino, T ;
Takemoto, Y .
ORGANIC LETTERS, 2001, 3 (21) :3329-3331
[43]   Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery [J].
Park, Young Jun ;
Park, Jung-Woo ;
Jun, Chul-Ho .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :222-234
[44]   Enantioselective catalytic hydroamination of alkenes [J].
Roesky, PW ;
Müller, TE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (24) :2708-2710
[45]   Enantioselective Bronsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines [J].
Rueping, M ;
Sugiono, E ;
Azap, C ;
Theissmann, T ;
Bolte, M .
ORGANIC LETTERS, 2005, 7 (17) :3781-3783
[46]   Theoretical study of the mechanism of Hantzsch ester hydrogenation of imines catalyzed by chiral BINOL-phosphoric acids [J].
Simon, Luis ;
Goodman, Jonathan M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8741-8747
[47]   Relay Catalysis by a Metal-Complex/Bronsted Acid Binary System in a Tandem Isomerization/Carbon-Carbon Bond Forming Sequence [J].
Sorimachi, Keiichi ;
Terada, Masahiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14452-+
[48]   Enantioselective organocatalytic reductive amination [J].
Storer, RI ;
Carrera, DE ;
Ni, Y ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :84-86
[49]   Gold(I)-Catalyzed Enantioselective Synthesis of Benzopyrans via Rearrangement of Allylic Oxonium Intermediates [J].
Uemura, Minoru ;
Watson, Iain D. G. ;
Katsukawa, Mikimoto ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) :3464-+
[50]   Asymmetric Synthesis of Medium-Sized Rings by Intramolecular Au(I)-Catalyzed Cyclopropanation [J].
Watson, Iain D. G. ;
Ritter, Stefanie ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2056-+