Synthesis of Tridentate Chiral Spiro Aminophosphine-Oxazoline Ligands and Application to Asymmetric Hydrogenation of α-Keto Amides

被引：24
作者：
Zhang, Feng-Hua [1 ,2 ]
Wang, Chen [1 ,2 ]
Xie, Jian-Hua [1 ,2 ]
Zhou, Qi-Lin [1 ,2 ,3 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elemento Organ Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 12期
基金：
中国国家自然科学基金;
关键词：
Tridentate ligand; Chiral Spiro catalyst; Asymmetric hydrogenation; Iridium; alpha-Keto amides; HIGHLY ENANTIOSELECTIVE HYDROGENATION; DIPHOSPHINE LIGANDS; CATALYZED HYDROGENATION; IRIDIUM CATALYSTS; COMPLEXES; BULKY; ACIDS; ALKYL;
D O I：
10.1002/adsc.201900251
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new type of tridentate chiral spiro aminophosphine-oxazoline ligands (SpiroOAP) have been synthesized through four steps. The SpiroOAP ligands are highly efficient for the asymmetric hydrogenation of alpha-keto amides, providing a variety of synthetically useful alpha-hydroxy amides with excellent enantioselectivity (up to 98% ee) and turnover numbers (up to 10,000).
引用
收藏
页码：2832 / 2835
页数：4
相关论文
共 46 条
  • [1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [2] [Anonymous], 1997, FLAV FRAGR, P185
  • [3] [Anonymous], 2013, ANGEW CHEM
  • [4] [Anonymous], 2017, Angew. Chem
  • [5] [Anonymous], 2011, ANGEW CHEM
  • [6] [Anonymous], 2015, Angew.Chem., DOI DOI 10.1002/ANGE.201502860
  • [7] [Anonymous], 2017, Angew. Chem
  • [8] Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of -Alkyl--Ketoesters
    Bao, Deng-Hui
    Wu, Hui-Ling
    Liu, Chao-Lun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8791 - 8794
  • [9] CharyMamillapalli N., 2015, ADV SYNTH CATAL, V357, P3273
  • [10] Enantioselective Hydrogenation and Transfer Hydrogenation of Bulky Ketones Catalysed by a Ruthenium Complex of a Chiral Tridentate Ligand
    Diaz-Valenzuela, M. Belen
    Phillips, Scott D.
    France, Marcia B.
    Gunn, Mary E.
    Clarke, Matthew L.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) : 1227 - 1232
12345