A SIMPLE ROUTE TO SYN ALPHA-AMINO-BETA-HYDROXY ESTERS BY C-2 REGIOSELECTIVE OPENING OF ALPHA,BETA-EPOXY ESTERS WITH METAL-HALIDES

被引：35
作者：
RIGHI, G [1 ]
RUMBOLDT, G [1 ]
BONINI, C [1 ]
机构：
[1] UNIV BASILICATA,DIPARTIMENTO CHIM,I-85100 POTENZA,ITALY
来源：
TETRAHEDRON | 1995年 / 51卷 / 48期
关键词：
D O I：
10.1016/0040-4020(95)00873-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha,beta-Epoxy esters are opened by NaX (X = I, Br) in a regio and stereoselective fashion to beta-hydroxy-alpha-halo esters, which represent suitable precursors of syn alpha-amino-beta-hydroxy esters and beta-hydroxy esters.
引用
收藏
页码：13401 / 13408
页数：8
相关论文
共 21 条
  • [1] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2
    BEHRENS, CH
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5696 - 5704
  • [2] C-1 REACTIVITY OF 2,3-EPOXY ALCOHOLS VIA OXIRANE OPENING WITH METAL-HALIDES - APPLICATIONS AND SYNTHESIS OF NATURALLY-OCCURRING 2,3-OCTANEDIOL, MURICATACIN, 3-OCTANOL, AND 4-DODECANOLIDE
    BONINI, C
    FEDERICI, C
    ROSSI, L
    RIGHI, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4803 - 4812
  • [3] AN EASY PROCEDURE FOR THE HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS
    BONINI, C
    GIULIANO, C
    RIGHI, G
    ROSSI, L
    [J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (13) : 1863 - 1870
  • [4] REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES
    BONINI, C
    RIGHI, G
    [J]. SYNTHESIS-STUTTGART, 1994, (03): : 225 - 238
  • [5] ENANTIOSELECTIVE AND STEREOSELECTIVE ROUTE TO THE TAXOL SIDE-CHAIN VIA ASYMMETRIC EPOXIDATION OF TRANS-CINNAMYL ALCOHOL AND SUBSEQUENT EPOXIDE RING-OPENING
    BONINI, C
    RIGHI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (24) : 2767 - 2768
  • [6] DIOLS OBTAINED VIA CHEMOSELECTIVE AND REGIOSELECTIVE RING-OPENING OF EPOXY ALCOHOLS - A STRAIGHTFORWARD SYNTHESIS OF 2S,3S-OCTANEDIOL
    BONINI, C
    RIGHI, G
    [J]. TETRAHEDRON, 1992, 48 (08) : 1531 - 1538
  • [7] BONINI C, 1994, TETRAHEDRON LETT, V35, P797
  • [8] BORDWELL FG, 1964, J AM CHEM SOC, V64, P4645
  • [9] CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34
  • [10] REGIOSELECTIVE OPENINGS OF 2,3-EPOXY ACIDS WITH ORGANOCUPRATES
    CHONG, JM
    SHARPLESS, KB
    [J]. TETRAHEDRON LETTERS, 1985, 26 (39) : 4683 - 4686
123