The highly diastereoselective synthesis of oxazolidines derived from ketones and pseudoephedrine or ephedrine

被引：7
|
作者：
Buckley, BR
Page, PCB [1 ]
Edgar, M
Elsegood, MRJ
Hayman, CM
Heaney, H
Rassias, GA
Talib, SA
Liddle, J
Readshaw, SA
Seaman, CJ
机构：
[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
[3] GlaxoSmithKline, Harlow CM19 5AW, Essex, England
来源：
SYNLETT | 2005年 / 06期
关键词：
amino alcohols; heterocycles; ketones; scandium; stereoselective;
D O I：
10.1055/s-2005-864824
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2,2-Dialkyl-3,4-dimethyl-5-phenyloxazolidines and 2-alkyl-2-aryl-3,4-dimethyl-5-phenyloxazolidines are formed with high diastereoselectivity from ketones and pseudoephedrine or ephedrine in the presence of scandium triflate and 4 A molecular sieves.
引用
收藏
页码：971 / 975
页数：5
相关论文
共 50 条
  • [1] Microwave-assisted highly diastereoselective synthesis of oxazolidines derived from ketones and aminoalcohols
    Page, Philip C. Bulman
    Parkes, Genna A.
    Buckley, Benjamin R.
    Heaney, Harry
    Gholizadeh, Mostafa
    Wailes, J. Steven
    TETRAHEDRON LETTERS, 2008, 49 (49) : 6951 - 6954
  • [2] A STUDY OF THE MASS-SPECTRA OF SOME OXAZOLIDINES DERIVED FROM EPHEDRINE AND PSEUDOEPHEDRINE
    WALKER, RB
    MASSEY, MD
    ORGANIC MASS SPECTROMETRY, 1988, 23 (03): : 215 - 216
  • [3] MASS-SPECTRA OF SOME OXAZOLIDINES FORMED BY REACTION OF EPHEDRINE AND PSEUDOEPHEDRINE WITH ALIPHATIC-KETONES
    WALKER, AB
    MOORE, DS
    MASSEY, MD
    ORGANIC MASS SPECTROMETRY, 1989, 24 (05): : 345 - 346
  • [4] EFFECTS OF OXAZOLIDINES DERIVED FROM (-) EPHEDRINE IN THE RAT
    WALKER, RB
    WOOD, DM
    AKMAL, MM
    SHARKS, E
    GENERAL PHARMACOLOGY, 1992, 23 (04): : 729 - 732
  • [5] FUSED HETEROCYCLES DERIVED FROM PSEUDOEPHEDRINE AND EPHEDRINE
    FARFAN, N
    SANTILLAN, RL
    CASTILLO, D
    CRUZ, R
    JOSEPHNATHAN, P
    DARAN, JC
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (11): : 2764 - 2770
  • [6] PHARMACOLOGICAL EFFECTS OF OXAZOLIDINES DERIVED FROM (-)EPHEDRINE IN RATS
    WALKER, RB
    WOOD, DM
    AKMAL, MM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 124 - MEDI
  • [7] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF AMINOALCOHOLS OF EPHEDRINE TYPE
    SOLLADIECAVALLO, A
    DREYFUS, AC
    SANCH, F
    KLEIN, A
    CHEMISTRY LETTERS, 1987, (08) : 1583 - 1586
  • [8] Oxazolidines from the reaction of (-) ephedrine and (+) pseudoephedrine with salicylaldehyde and p-hydroxybenzaldehyde and their rates of hydrolysis
    Bourne S.A.
    Fitz L.D.
    Kashyap R.P.
    Krawiec M.
    Walker R.B.
    Watson W.H.
    Williams L.M.
    Journal of Chemical Crystallography, 1997, 27 (1) : 35 - 44
  • [9] Oxazolidines from the reaction of (-) ephedrine and (+) pseudoephedrine with salicylaldehyde and p-hydroxybenzaldehyde and their rates of hydrolysis
    Bourne, SA
    Fitz, LD
    Kashyap, RP
    Krawiec, M
    Walker, RB
    Watson, WH
    Williams, LM
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (01) : 35 - 44
  • [10] N-BORANE ADDUCTS OF OXAZOLIDINES DERIVED FROM EPHEDRINE AND PSEUDOEPHEDRINE - STUDY OF STEREOCHEMISTRY BY NUCLEAR MAGNETIC-RESONANCE
    CONTRERAS, R
    SANTIESTEBAN, F
    PAZSANDOVAL, MA
    WRACKMEYER, B
    TETRAHEDRON, 1984, 40 (19) : 3829 - 3838
12345