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
  • [31] H-1-NMR SPECTRA OF BETA-ALCOHOL DERIVED FROM EPHEDRINE AND CORRESPONDING OXAZOLIDINES
    BAUDET, M
    GELBCKE, M
    ANALYTICAL LETTERS, 1979, 12 (04) : 325 - 338
  • [32] ION-SPRAY MASS-SPECTRA AND DAUGHTER ION ANALYSIS OF OXAZOLIDINES DERIVED FROM EPHEDRINE
    WALKER, RB
    BAKHTIAR, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 214 - MEDI
  • [33] Synthesis of Oxazolidines and Dihydroxazines via Cyclization of α-Aminated Ketones
    Sun, Mingze
    Chen, Jingjing
    Ding, Zhenhua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 10647 - 10654
  • [34] Highly diastereoselective addition of allyltitanocenes to α-chiral ketones
    Takeda, Takeshi
    Yoshida, Satoshi
    Nishimura, Takuya
    Tsubouchi, Akira
    TETRAHEDRON LETTERS, 2012, 53 (30) : 3930 - 3933
  • [35] Rh2(OAc)4 catalyzed highly diastereoselective synthesis of 2,4,5-triaryl-1,3-oxazolidines and spirooxindolyl oxazolidines
    Rajasekaran, Tamilselvan
    Sridhar, B.
    Reddy, B. V. Subba
    TETRAHEDRON, 2016, 72 (17) : 2102 - 2108
  • [36] ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE WITH 1,3,2-OXAZABOROLIDINES DERIVED FROM EPHEDRINE, PSEUDOEPHEDRINE, AND PHENYLGLYCINE
    BERENGUER, R
    GARCIA, J
    GONZALEZ, M
    VILARRASA, J
    TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 13 - 16
  • [37] An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine
    Martinez, R. Fernando
    Avalos, Martin
    Babiano, Reyes
    Cintas, Pedro
    Jimenez, Jos L.
    Light, Mark E.
    Palacios, Juan C.
    Perez, Esther M. S.
    TETRAHEDRON, 2008, 64 (27) : 6377 - 6386
  • [38] THE STANDARD ENTHALPIES OF COMBUSTION AND FORMATION OF BIOXAZOLIDINE AND CIS-OXAZINO-OXAZINES DERIVED FROM PSEUDOEPHEDRINE AND EPHEDRINE
    TORRES, LA
    GUDINO, R
    HERNANDEZCONTRERAS, I
    OCHOA, ME
    FARFAN, N
    SANTILLAN, RL
    JOURNAL OF CHEMICAL THERMODYNAMICS, 1995, 27 (07): : 779 - 786
  • [39] The standard enthalpies of combustion and formation of bioxazolidine and cis-oxazino-oxazines derived from pseudoephedrine and ephedrine
    1600, (16):
  • [40] Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines
    Page, Philip C. Bulman
    Buckley, Benjamin R.
    Elsegood, Mark R. J.
    Hayman, Colin M.
    Heaney, Harry
    Rassias, Gerasimos A.
    Talib, Salem A.
    Liddle, John
    TETRAHEDRON, 2007, 63 (45) : 10991 - 10999
12345