A new method for preparation of 3,6-dihydro-2H-1,3-oxazines and explorations of their use in stereoselective synthesis of 1,3-amino alcohol derivatives

被引:14
|
作者
Cherkauskas, JP
Klos, AM
Borzilleri, RM
Sisko, J
Weinreb, SM
Parvez, M
机构
[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802
[2] UNIV CALGARY,DEPT CHEM,CALGARY,AB T2N 1N4,CANADA
关键词
D O I
10.1016/0040-4020(95)01100-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Condensation of P-hydroxy aldehydes with N-sulfonyl aldimines produces 3,6-dihydro-2H-1,3-oxazines in moderate to excellent yields. The process is stereoselective, with the C-2 and C-6 substituents having a trans relationship in these heterocycles. Some transformations of these oxazines as potential acyclic 1,3-amino alcohol synthons are described.
引用
收藏
页码:3135 / 3152
页数:18
相关论文
共 50 条
  • [2] PREPARATION OF 3,6-DIHYDRO-2H-1,3-OXAZINES AND THEIR USE AS POTENTIAL 1,3-AMINO ALCOHOL SYNTHONS
    CHERKAUSKAS, JP
    BORZILLERI, RM
    SISKO, J
    WEINREB, SM
    SYNLETT, 1995, (05) : 527 - 528
  • [3] SYNTHESIS OF 1,3-AMINO ALCOHOLS FROM 2-AZA-1,3-DIENES BY REDUCTION OF 5,6-DIHYDRO-2H-1,3-OXAZINES
    BARLUENGA, J
    JOGLAR, J
    GONZALEZ, FJ
    FUSTERO, S
    KRUGER, C
    TSAY, YH
    SYNTHESIS-STUTTGART, 1991, (05): : 387 - 393
  • [4] SYNTHESIS OF SUBSTITUTED "2-AMINO-5,6-DIHYDRO-4H-1,3-OXAZINES AND 2-IMINOTETRAHYDRO-1,3-OXAZINES
    IGNATOVA, LA
    GEKHMAN, AE
    OVECHKIN, PL
    UNKOVSKI.BV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1974, (03): : 354 - 356
  • [5] Synthesis of alicyclic N-substituted 1,3-amino alcohols via 1,3-oxazines
    Balazs, Arpad
    Szakonyi, Zsolt
    Fueloep, Ferenc
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (02) : 403 - 406
  • [6] Ytterbium Triflate Promoted One-Pot Three Component Synthesis of 3,4,5-Trisubstituted-3,6-dihydro-2H-1,3-oxazines
    Francesco Epifano
    Caroline Pelucchini
    Ornelio Rosati
    Salvatore Genovese
    Massimo Curini
    Catalysis Letters, 2011, 141 : 844 - 849
  • [7] Ytterbium Triflate Promoted One-Pot Three Component Synthesis of 3,4,5-Trisubstituted-3,6-dihydro-2H-1,3-oxazines
    Epifano, Francesco
    Pelucchini, Caroline
    Rosati, Ornelio
    Genovese, Salvatore
    Curini, Massimo
    CATALYSIS LETTERS, 2011, 141 (06) : 844 - 849
  • [8] SYNTHESIS OF SUBSTITUTED "2-AMINO-5,6-DIHYDRO-4H-1,3-OXAZINES
    IGNATOV, LA
    UNKOVSKI.BV
    BRANZBUR.MZ
    GEKHMAN, AE
    OVECHKIN, PL
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1972, (08): : 1037 - &
  • [9] Simple synthesis of 2H-1,3-oxazines and their stereoselective transformation into 1,3-aminoalcohols and azetidines
    Barluenga, J
    Tomas, M
    Ballesteros, A
    Kong, JS
    TETRAHEDRON, 1996, 52 (09) : 3095 - 3106
  • [10] SYNTHESIS OF SUBSTITUTED 2-AMINO-4H-1,3-OXAZINES
    IGNATOVA, LA
    GEKHMAN, AE
    SPEKTOR, MA
    OVECHKIN, PL
    UNKOVSKI.BV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1974, (06): : 764 - 767