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
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
  • [1] A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides
    Andersen, NG
    Ramsden, PD
    Che, DQ
    Parvez, M
    Keay, BA
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22): : 7478 - 7486
  • [2] The resolution and application of P-stereogenic phosphine oxides
    Bagi, Peter
    Herbay, Reka
    Juhasz, Kinga
    Varga, Bence
    Fogassy, Elemer
    Keglevich, Gyoergy
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (11-12) : 1459 - 1461
  • [3] Dynamic resolution of P-stereogenic phosphine oxides with choice of enantiomer in the work-up
    Nikitin, Kirill
    Jennings, Elizabeth V.
    Rajendran, Kamalraj V.
    Gilheany, Declan G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [4] Asymmetric Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs)
    Glueck, David S.
    SYNTHESIS-STUTTGART, 2022, 54 (02): : 271 - 280
  • [5] Enantioseparation of P-Stereogenic Secondary Phosphine Oxides and Their Stereospecific Transformation to Various Tertiary Phosphine Oxides and a Thiophosphinate
    Varga, Bence
    Szemesi, Peter
    Nagy, Petra
    Herbay, Reka
    Holczbauer, Tamas
    Fogassy, Elemer
    Keglevich, Gyorgy
    Bagi, Peter
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14493 - 14507
  • [6] Experimental and Theoretical Investigations of the Stereoselective Synthesis of P-Stereogenic Phosphine Oxides
    Copey, Laurent
    Jean-Gerard, Ludivine
    Framery, Eric
    Pilet, Guillaume
    Robert, Vincent
    Andrioletti, Bruno
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (25) : 9057 - 9061
  • [7] Desymmetrization by metathesis, producing enantioenriched P-stereogenic phosphine oxides.
    Bisaro, F
    Gouverneur, V
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U376 - U376
  • [8] D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides
    D'Onofrio, A.
    Copey, L.
    Jean-Gerard, L.
    Goux-Henry, C.
    Pilet, G.
    Andrioletti, B.
    Framery, E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (34) : 9029 - 9034
  • [9] Preparation of Optically Pure Tertiary Phosphine Oxides via the Addition of P-Stereogenic Secondary Phosphine Oxide to Activated Alkenes
    Wang, Ji-Ping
    Nie, Shao-Zhen
    Zhou, Zhong-Yang
    Ye, Jing-Jing
    Wen, Jing-Hong
    Zhao, Chang-Qiu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 7644 - 7653
  • [10] P-Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides
    Mohd, Aabid
    Anitha, Thippani
    Reddy, Kallu Rajender
    Wencel-Delord, Joanna
    Colobert, Francoise
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (48) : 7836 - 7841