Enantioselective Preparation of P-Chiral Phosphine Oxides

被引：59
|
作者：
Adams, Harry [1 ]
Collins, Rebecca C. [1 ]
Jones, Simon [1 ]
Warner, Christopher J. A. [1 ]
机构：
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 24期
基金：
英国工程与自然科学研究理事会;
关键词：
CATALYTIC ASYMMETRIC DEPROTONATION; KINETIC RESOLUTION; STEREOGENIC COMPOUNDS; PHOSPHORUS-COMPOUNDS; LIGANDS; BORANES; ROUTE; ORGANOCATALYSTS; DIPHOSPHINES; AUXILIARIES;
D O I：
10.1021/ol202916j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient chiral auxiliary-based strategy for the asymmetric synthesis of P-chiral phosphine oxides in >98:2 er has been developed. The methodology involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides.
引用
收藏
页码：6576 / 6579
页数：4
相关论文
共 50 条
  • [41] P-Chiral phosphine oxide catalysed reduction of prochiral ketimines using trichlorosilane
    Warner, Christopher J. A.
    Reeder, Andrew T.
    Jones, Simon
    TETRAHEDRON-ASYMMETRY, 2016, 27 (2-3) : 136 - 141
  • [42] Highly stereoselective, thermodynamically controlled and reversible formation of a new P-chiral phosphine
    Komarov, IV
    Spannenberg, A
    Holz, J
    Börner, A
    CHEMICAL COMMUNICATIONS, 2003, (17) : 2240 - 2241
  • [43] Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine P-Sulfides as a Route to P-Chiral Catalysts
    Madalinska, Lidia
    Kielbasinski, Piotr
    Kwiatkowska, Malgorzata
    CATALYSTS, 2022, 12 (02)
  • [44] Synthesis of P-Chiral Tertiary Phosphine Oxides by Copper-Catalyzed Dynamic Kinetic Asymmetric C-P Cross-Coupling
    Kang, Jie
    Ren, Simu
    Su, Bo
    SYNLETT, 2024, 35 (07) : 741 - 746
  • [45] P-chiral phosphine ligands for transition-metal-catalyzed asymmetric reactions
    Imamoto, Tsuneo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (11) : 1060 - 1069
  • [46] P-chiral bis(trialkylphosphine) ligands and their use in highly enantioselective hydrogenation reactions
    Imamoto, T
    Watanabe, J
    Wada, Y
    Masuda, H
    Yamada, H
    Tsuruta, H
    Matsukawa, S
    Yamaguchi, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) : 1635 - 1636
  • [47] OxaPhos: A new class of tunable, P-chiral, monodentate ligands for enantioselective catalysis
    Schuster, Christopher H.
    Morken, James P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [48] Enantioselective chlorinative aldol reaction of α-substituted acroleins catalyzed by chiral phosphine oxides
    Kotani, Shunsuke
    Hanamure, Takuya
    Nozaki, Hirono
    Sugiura, Masaharu
    Nakajima, Makoto
    TETRAHEDRON-ASYMMETRY, 2017, 28 (02) : 282 - 287
  • [49] Enantioselective hydrogenation of ketones by iridium nanoparticles ligated with chiral secondary phosphine oxides
    Cano, Israel
    Tschan, Mathieu J. -L.
    Martinez-Prieto, Luis M.
    Philippot, Karine
    Chaudret, Bruno
    van Leeuwen, Piet W. N. M.
    CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (11) : 3758 - 3766
  • [50] Redox-Switchable Transfer Hydrogenations with P-Chiral Dendritic Ferrocenyl Phosphine Complexes
    Popp, John
    Caminade, Anne-Marie
    Hey-Hawkins, Evamarie
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (17) : 1654 - 1669
12345