Enantioselective Synthesis of α-Chiral Amides by Catalytic Hydrogenation with Iridium N,P-Complexes

被引:2
|
作者
Peters, Bram B. C. [1 ]
Birke, Norman [1 ]
Massaro, Luca [1 ]
Andersson, Pher G. [1 ,2 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Svante Arrhenius vag 16C, S-10691 Stockholm, Sweden
[2] Univ Kwazulu Natal, Sch Chem & Phys, Private Bag X54001, ZA-4000 Durban, South Africa
基金
瑞典研究理事会;
关键词
amides; enantioselectivity; iridium catalysis; asymmetric catalysis; hydrogenation; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; MINIMALLY FUNCTIONALIZED OLEFINS; ASYMMETRIC HYDROGENATION; LIGANDS; ALKYLATION; ALDOL; ENANTIOCONVERGENT; AMIDATION; LACTAMS; NMR;
D O I
10.1055/s-0042-1751399
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic asymmetric hydrogenation of olefins constitutes a powerful method for the preparation of chiral compounds. A series of prochiral unsaturated amides were efficiently reduced with high enantioselectivities by means of an iridium N,P-complex-catalyzed hydrogenation. Its application in the synthesis of fenpropidin and the possibility of using isomeric mixtures of starting materials are attractive features of the method
引用
收藏
页码:1519 / 1523
页数:5
相关论文
共 50 条
  • [21] HOMOGENEOUS ENANTIOSELECTIVE HYDROGENATION WITH CHIRAL ORGANOLANTHANIDE COMPLEXES
    CONTICELLO, VP
    BRARD, L
    GIARDELLO, MA
    TSUJI, Y
    SABAT, M
    MARKS, TJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 31 - INOR
  • [23] Synthesis of a key intermediate of levofloxacin via enantioselective hydrogenation catalyzed by iridium(I) complexes
    Satoh, K
    Inenaga, M
    Kanai, K
    TETRAHEDRON-ASYMMETRY, 1998, 9 (15) : 2657 - 2662
  • [24] Highly enantioselective transfer hydrogenation of aromatic ketones catalyzed by chiral diaminodiphosphine-iridium(I) complexes
    Tang, CL
    Li, YY
    Pan, ED
    Zhang, H
    Zhou, ZH
    Gao, JX
    ACTA CHIMICA SINICA, 2001, 59 (10) : 1831 - 1834
  • [25] Enantioselective Hydrogenation of a-Substituted Acrylic Acids Catalyzed by Iridium Complexes with Chiral Spiro Aminophosphine Ligands
    Zhu, Shou-Fei
    Yu, Yan-Bo
    Li, Shen
    Wang, Li-Xin
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (35) : 8872 - 8875
  • [26] Asymmetric Cyclization of N-Sulfonyl Alkenyl Amides Catalyzed by Iridium/Chiral Diene Complexes
    Nagamoto, Midori
    Yanagi, Tomoyuki
    Nishimura, Takahiro
    Yorimitsu, Hideki
    ORGANIC LETTERS, 2016, 18 (18) : 4474 - 4477
  • [27] Enantioselective Hydrogenation of Diarylmethanimines for Synthesis of Chiral Diarylmethylamines
    Kong, Duanyang
    Li, Meina
    Zi, Guofu
    Hou, Guohua
    He, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6640 - 6648
  • [28] Iridium-Catalyzed Asymmetric Hydrogenation of Olefins with Chiral N,P and C,N Ligands
    Woodmansee, David H.
    Pfaltz, Andreas
    IRIDIUM CATALYSIS, 2011, 34 : 31 - +
  • [29] Catalytic enantioselective synthesis of chiral tetraarylmethanes
    Li, Xingguang
    Duan, Meng
    Deng, Zhiqin
    Shao, Qianzhen
    Chen, Min
    Zhu, Guangyu
    Houk, K. N.
    Sun, Jianwei
    NATURE CATALYSIS, 2020, 3 (12) : 1010 - 1019
  • [30] Catalytic Enantioselective Synthesis of Chiral γ-Butyrolactones
    Yanagisawa, Akira
    Kushihara, Naoyuki
    Yoshida, Kazuhiro
    ORGANIC LETTERS, 2011, 13 (06) : 1576 - 1578