Intramolecular reaction of gamma-alkoxyallylstannane with hydrazone: Stereoselective synthesis of beta-aminotetrahydro-pyran and -furan

被引:12
作者
Kadota, I [1 ]
Park, JY [1 ]
Yamamoto, Y [1 ]
机构
[1] TOHOKU UNIV,GRAD SCH SCI,DEPT CHEM,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1039/cc9960000841
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Lewis acid mediated cyclization of gamma-oxygen substituted allylic stannanes 1, 2 and 9, bearing a hydrazone group at the terminus of the carbon chain, afforded the corresponding trans-beta-amino cyclic ethers 3a, 4a and 10, respectively, with very high diastereoselectivities in high chemical yields.
引用
收藏
页码:841 / 842
页数:2
相关论文
共 15 条
  • [1] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS
    ALVAREZ, E
    CANDENAS, ML
    PEREZ, R
    RAVELO, JL
    MARTIN, JD
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1953 - 1980
  • [2] SIMPLE DESIGNS FOR THE CONSTRUCTION OF COMPLEX TRANS-FUSED POLYETHER TOXIN FRAMEWORKS - A LINEAR STRATEGY BASED ON ENTROPICALLY FAVORED OXIRANE RING ENLARGEMENT IN EPOXYCYCLOALKENES FOLLOWED BY CARBON-CARBON OR CARBON-OXYGEN BOND-FORMING CYCLIZATIONS
    ALVAREZ, E
    DIAZ, MT
    PEREZ, R
    RAVELO, JL
    REGUEIRO, A
    VERA, JA
    ZURITA, D
    MARTIN, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2848 - 2876
  • [3] CATALYTIC ALLYLATION OF IMINES PROMOTED BY LANTHANIDE TRIFLATES
    BELLUCCI, C
    COZZI, PG
    UMANIRONCHI, A
    [J]. TETRAHEDRON LETTERS, 1995, 36 (40) : 7289 - 7292
  • [4] CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION
    GEVORGYAN, V
    KADOTA, I
    YAMAMOTO, Y
    [J]. TETRAHEDRON LETTERS, 1993, 34 (08) : 1313 - 1316
  • [5] KADOTA I, 1995, TETRAHEDRON LETT, V36, P5777, DOI 10.1016/0040-4039(95)01097-2
  • [6] STEREOCONTROLLED SYNTHESIS OF THE HEMIBREVETOXIN RING-SYSTEM VIA AN ALLYLIC TIN METHOD
    KADOTA, I
    MATSUKAWA, Y
    YAMAMOTO, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (21) : 1638 - 1641
  • [7] KLEINMAN EF, 1991, COMPREHENSIVE ORGANI, V2, P957
  • [8] NEW SYNTHETIC STRATEGY FOR THE CONSTRUCTION OF TRANSFUSED MEDIUM-SIZED CYCLIC ETHERS - SYNTHESIS OF THE IJK FRAMEWORK OF THE POLYETHER CIGUATOXIN
    RAVELO, JL
    REGUEIRO, A
    MARTIN, JD
    [J]. TETRAHEDRON LETTERS, 1992, 33 (23) : 3389 - 3392
  • [9] SAMARIUM(II) IODIDE INDUCED RADICAL CYCLIZATIONS OF HALOHYDRAZONE AND CARBONYLHYDRAZONE
    STURINO, CF
    FALLIS, AG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) : 7447 - 7448
  • [10] ENANTIOSELECTIVE SYNTHESIS OF THE AB-RING FRAGMENT OF GAMBIERTOXIN-4B - IMPLICATION FOR THE ABSOLUTE-CONFIGURATION OF GAMBIERTOXIN-4B AND CIGUATOXIN
    SUZUKI, T
    SATO, O
    HIRAMA, M
    YAMAMOTO, Y
    MURATA, M
    YASUMOTO, T
    HARADA, N
    [J]. TETRAHEDRON LETTERS, 1991, 32 (35) : 4505 - 4508