Pd-catalyzed asymmetric allylic amination using easily accessible metallocenyl P,N-ligands

被引:15
|
作者
Wu, Hongwei [1 ]
Xie, Fang [1 ]
Wang, Yanlan [1 ]
Zhao, Xiaohu [1 ]
Liu, Delong [2 ]
Zhang, Wanbin [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE SYNTHESIS; PLANAR CHIRALITY; BISPHOSPHINE LIGANDS; CYCLOBUTANE BACKBONE; DIPHOSPHINE LIGANDS; RUPHOX-RU; ALKYLATION; PHOSPHINE; SUBSTITUTION; FERROCENE;
D O I
10.1039/c5ob00032g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compared to their C-1-symmetric counterparts, planar chiral C-2-symmetric metallocenyl P,N-ligands are efficient chiral ligands for Pd-catalyzed asymmetric allylic aminations, providing a number of amination products with high enantioselectivities. A non-C-2-symmetric ferrocenyl P,N-ligand (a by-product obtained during the synthesis of the above C-2-symmetric species) was also found to be an efficient ligand for asymmetric allylic aminations. A mixed ligand system consisting of both C-2- and non-C-2-symmetric ferrocene complexes was examined and showed high catalytic activity with the amination products being obtained with excellent enantioselectivities.
引用
收藏
页码:4248 / 4254
页数:7
相关论文
共 50 条
  • [1] Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions
    Qin Hao
    Hou Chuanjin
    Liang Dinghua
    He Xinwei
    Li Ling
    Hu Xiangping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 282 - 290
  • [2] Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands
    Johansson, Charlotte
    Lloyd-Jones, Guy C.
    Norrby, Per-Ola
    TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1585 - 1592
  • [3] Highly regio- and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands
    You, SL
    Zhu, XZ
    Luo, YM
    Hou, XL
    Dai, LX
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) : 7471 - 7472
  • [4] Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation
    Jiang, Biao
    Huang, Zuo-Gang
    Cheng, Ke-Jun
    TETRAHEDRON-ASYMMETRY, 2006, 17 (06) : 942 - 951
  • [5] Palladium-catalyzed asymmetric allylic alkylation using chiral P,N-ligands
    Mino, T
    Tanaka, Y
    Sakamoto, M
    Fujita, T
    HETEROCYCLES, 2000, 53 (07) : 1485 - 1488
  • [6] Kinetic Resolution of Indolines by Pd-Catalyzed Asymmetric Allylic Amination
    Hou, Xue Long
    Zheng, Bao Hui
    ORGANIC LETTERS, 2009, 11 (08) : 1789 - 1791
  • [8] First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands
    Blochl, PE
    Togni, A
    ORGANOMETALLICS, 1996, 15 (20) : 4125 - 4132
  • [9] Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation
    Kim, Kyoung Hoon
    Jeong, Chan-Kyu
    Kim, Do-Hoon
    Ha, Deok-Chan
    TETRAHEDRON-ASYMMETRY, 2006, 17 (11) : 1688 - 1692
  • [10] Pd-catalyzed asymmetric allylic alkylation using furanoside diphosphinite ligands
    Guimet, E
    Diéguez, M
    Ruiz, A
    Claver, C
    INORGANICA CHIMICA ACTA, 2005, 358 (13) : 3824 - 3828