Oxidative cleavage of unsaturated 1,2-diols using chiral lead-tetracarboxylates obtained by in situ metathesis

被引：0
|
作者：
Lena, JIC [1 ]
Sesenoglu, Ö [1 ]
Birlirakis, N [1 ]
Arseniyadis, S [1 ]
机构：
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 01期
关键词：
ring expansion; cascade transformations; acetate metathesis; chiral carboxylic solvents;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A combination of an acetate metathesis/cascade transformations process, providing ring enlarged systems decorated with a chiral auxiliary, is presented. The use of a chiral carboxylic acid, such as (S)-2-acetoxypropionic acid, gives diastereomeric mixtures when performed in the racemic series, offering the possibility of a chemical resolution. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码：21 / 24
页数：4
相关论文
共 39 条
  • [1] OXIDATIVE CLEAVAGE OF 1,2-DIOLS WITH N-IODOSUCCINIMIDE
    BEEBE, TR
    HII, P
    REINKING, P
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09): : 1927 - 1929
  • [2] Simple metal-free oxidative cleavage of 1,2-diols
    Dorado, Vicente
    Herrerias, Clara I.
    Fraile, Jose M.
    TETRAHEDRON, 2023, 139
  • [3] Pb(OAc)4 mediated oxidative cleavage of steroidal unsaturated 1,2-diols:: influence of the angular substitution
    Ferreira, MDR
    Hernando, JIM
    Lena, JIC
    Toupet, L
    Birlirakis, N
    Arseniyadis, S
    TETRAHEDRON LETTERS, 1999, 40 (43) : 7679 - 7682
  • [4] Oxidative cleavage of 1,2-diols, α-ketols and 1,2-diketones with aqueous sodium hypochlorite
    Khurana, J. M.
    Sharma, P.
    Gogia, A.
    Kandpal, B. M.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2007, 39 (02) : 185 - 189
  • [5] SILVER(I)-CATALYZED OXIDATIVE CLEAVAGE REACTIONS OF CYCLIC 1,2-DIOLS BY PEROXYDISULFATE
    HUYSER, ES
    ROSE, LG
    JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (06): : 851 - &
  • [6] EcoMnOx, a Biosourced Catalyst for Selective Aerobic Oxidative Cleavage of Activated 1,2-Diols
    Escande, Vincent
    Lam, Chun Ho
    Grison, Claude
    Anastas, Paul T.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (04): : 3214 - 3222
  • [7] A NEW AND EFFICIENT HETEROGENEOUS SYSTEM FOR THE OXIDATIVE CLEAVAGE OF 1,2-DIOLS AND THE OXIDATION OF HYDROQUINONES
    DAUMAS, M
    VOQUANG, Y
    VOQUANG, L
    LEGOFFIC, F
    SYNTHESIS-STUTTGART, 1989, (01): : 64 - 65
  • [8] Mechanistic aspects of the electrocatalytic oxidative cleavage of 1,2-diols by electrogenerated Pb(IV)
    Marken, F
    Squires, AM
    Alden, JA
    Compton, RG
    Buston, JEH
    Moloney, MG
    JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (07): : 1186 - 1192
  • [9] OXIDATIVE CLEAVAGE OF 1,2-DIOLS TO CARBOXYLIC-ACIDS BY HYDROGEN-PEROXIDE
    VENTURELLO, C
    RICCI, M
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09): : 1599 - 1602
  • [10] OXIDATIVE C-C BOND-CLEAVAGE OF 1,2-DIOLS BY SILVER(II)
    KUMAR, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (17) : 5179 - 5182
1234