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
来源：
TETRAHEDRON | 1996年 / 52卷 / 09期
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 30 条
  • [1] ADAM W, 1991, CHEM BER, V124, P237
  • [2] CARBON-CARBON BOND FORMATION VIA N-TOSYLIMINIUM IONS
    AHMAN, J
    SOMFAI, P
    [J]. TETRAHEDRON, 1992, 48 (43) : 9537 - 9544
  • [3] AHMAN J, 1992, TETRAHEDRON LETT, V33, P3791
  • [4] HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE
    ALBRECHT, R
    KRESZE, G
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05): : 1431 - &
  • [5] ARYLSULFONYLIMINE - DARSTELLUNG EIGENSCHAFTEN UND REAKTIVITAT
    ALBRECHT, R
    KRESZE, G
    MLAKAR, B
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (02): : 483 - &
  • [6] ALDER B, 1978, J PRAKT CHEM, P904
  • [7] A GENERAL-METHOD FOR THE REDUCTIVE CARBAMATION AND SULFONAMIDATION OF ALDEHYDES
    ALEXANDER, MD
    ANDERSON, RE
    SISKO, J
    WEINREB, SM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) : 2563 - 2564
  • [8] STEREOSELECTIVE SYNTHESIS OF 1,3-AMINO ALCOHOLS AND 1,3-AMINO KETONES
    BARLUENGA, J
    AGUILAR, E
    FUSTERO, S
    OLANO, B
    VIADO, AL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) : 1219 - 1223
  • [9] 1,3-AMINO ALCOHOLS FROM 4-AMINO-1-AZA DIENES - DIASTEREOSELECTIVE AND ENANTIOSELECTIVE APPROACH TO THE 4 DIASTEREOISOMERS OF THE N-TERMINAL AMINO-ACID COMPONENT OF NIKKOMYCIN-B AND NIKKOMYCIN-B(X)
    BARLUENGA, J
    VIADO, AL
    AGUILAR, E
    FUSTERO, S
    OLANO, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 5972 - 5975
  • [10] CONVENIENT PROCEDURE FOR THE REDUCTION OF BETA-ENAMINO KETONES - SYNTHESIS OF GAMMA-AMINO ALCOHOLS AND TETRAHYDRO-1,3-OXAZINES
    BARTOLI, G
    CIMARELLI, C
    PALMIERI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05): : 537 - 543
123