A novel resolution procedure for the preparation of P-stereogenic phosphine oxides

被引：25
|
作者：
Andersen, NG [1 ]
Ramsden, PD [1 ]
Che, DQ [1 ]
Parvez, M [1 ]
Keay, BA [1 ]
机构：
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
来源：
ORGANIC LETTERS | 1999年 / 1卷 / 12期
关键词：
D O I：
10.1021/ol991174s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.
引用
收藏
页码：2009 / 2011
页数：3
相关论文
共 50 条
  • [31] P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis
    Su, Hsin Y.
    Taylor, Mark S.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06): : 3173 - 3182
  • [32] The resolution of acyclic P-stereogenic phosphine oxides via the formation of diastereomeric complexes: A case study on ethyl-(2-methylphenyl)-phenylphosphine oxide
    Bagi, Peter
    Varga, Bence
    Szilagyi, Andras
    Karaghiosoff, Konstantin
    Czugler, Matyas
    Fogassy, Elemer
    Keglevich, Gyorgy
    CHIRALITY, 2018, 30 (04) : 509 - 522
  • [33] Synthesis of Enantiopure P-Stereogenic Diphosphacrowns using P-Stereogenic Secondary Phosphines
    Morisaki, Yasuhiro
    Kato, Ryosuke
    Chujo, Yoshike
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2769 - 2774
  • [34] Nucleophilic Substitution of P-Stereogenic Chlorophosphines: Mechanism, Stereochemistry, and Stereoselective Conversions of Diastereomeric Secondary Phosphine Oxides to Tertiary Phosphines
    Ye, Jing-Jing
    Nie, Shao-Zhen
    Wang, Ji-Ping
    Wen, Jing-Hong
    Zhang, Yu
    Qiu, Mao-Ran
    Zhao, Chang-Qu
    ORGANIC LETTERS, 2017, 19 (19) : 5384 - 5387
  • [35] Enantioselective Synthesis of P-Stereogenic Phosphinates and Phosphine oxides by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis
    Harvey, James Stephen
    Malcolmson, Steven J.
    Dunne, Katherine S.
    Meek, Simon J.
    Thompson, Amber L.
    Schrock, Richard R.
    Hoveyda, Amir H.
    Gouverneur, Veronique
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) : 762 - 766
  • [36] Synthesis of P-Stereogenic Diarylphosphinamides as Novel Inhibitors of Melanoma
    Xu Tang
    Zhijun Du
    Guojie Wu
    Fushe Han
    Chemical Research in Chinese Universities, 2019, 35 : 812 - 816
  • [37] Synthesis of P-Stereogenic Diarylphosphinamides as Novel Inhibitors of Melanoma
    Tang Xu
    Du Zhijun
    Wu Guojie
    Han Fushe
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2019, 35 (05) : 812 - 816
  • [38] Catalytic asymmetric deprotonation of phosphine boranes and sulfides as a route to P-stereogenic compounds
    Gammon, Jonathan J.
    Canipa, Steven J.
    O'Brien, Peter
    Kelly, Brian
    Taylor, Sven
    CHEMICAL COMMUNICATIONS, 2008, (32) : 3750 - 3752
  • [39] Regioselective Lithiation of Silyl Phosphine Sulfides: Asymmetric Synthesis of P-Stereogenic Compounds
    Gammon, Jonathan J.
    O'Brien, Peter
    Kelly, Brian
    ORGANIC LETTERS, 2009, 11 (21) : 5022 - 5025
  • [40] Preparation of optically pure P-stereogenic trivalent phosphorus compounds
    Grabulosa, Arnald
    Granell, Jaume
    Muller, Guillermo
    COORDINATION CHEMISTRY REVIEWS, 2007, 251 (1-2) : 25 - 90
12345