STEREOSPECIFICITY AND STEREOSELECTIVITY IN THE [3,2] SIGMATROPIC REARRANGEMENT OF OPEN-CHAIN SULFONIUM YLIDES

被引：11
|
作者：
HARTLEY, RC
WARREN, S
机构：
[1] UNIV CAMBRIDGE,CHEM LABS,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND
[2] SCHERING AGROCHEM LTD,CHESTERFORD PK RES STN,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 52期
关键词：
D O I：
10.1016/S0040-4039(00)74746-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The [3,2] sigmatropic rearrangement of sulphonium ylides derived from allyl sulphides with 1,2-related chiral centres was carried out with excellent stereochemical control. 1,4-Related chiral centres across an E double bond are set up stereospecifically by this reaction and good 4,5 diastereoselectivity is observed.
引用
收藏
页码：8155 / 8158
页数：4
相关论文
共 50 条
  • [1] Lending a hand to asymmetric trifluoromethylthiolation:enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Guoliang Mao
    Lei Chen
    Congyang Wang
    [J]. Science China Chemistry, 2017, (12) : 1565 - 1566
  • [2] Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Zhang, Zhikun
    Sheng, Zhe
    Yu, Weizhi
    Wu, Guojiao
    Zhang, Rui
    Chu, Wen-Dao
    Zhang, Yan
    Wang, Jianbo
    [J]. NATURE CHEMISTRY, 2017, 9 (10) : 970 - 976
  • [3] Lending a hand to asymmetric trifluoromethylthiolation:enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Guoliang Mao
    Lei Chen
    Congyang Wang
    [J]. Science China(Chemistry)., 2017, 60 (12) - 1566
  • [4] [2,3]-Wittig sigmatropic rearrangement of alpha-phosphonylated sulfonium and ammonium ylides
    Makomo, H
    Saquet, M
    Simeon, F
    Masson, S
    AboutJaudet, E
    Collignon, N
    GuleaPurcarescu, M
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 109 (1-4) : 445 - 448
  • [5] Lending a hand to asymmetric trifluoromethylthiolation: enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Mao, Guoliang
    Chen, Lei
    Wang, Congyang
    [J]. SCIENCE CHINA-CHEMISTRY, 2017, 60 (12) : 1565 - 1566
  • [6] [2,3]-SIGMATROPIC REARRANGEMENT OF SULFUR YLIDES DERIVED FROM TRIMETHYLSILYL SULFONIUM SALTS
    PADWA, A
    GASDASKA, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14): : 2857 - 2858
  • [7] Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Zhikun Zhang
    Zhe Sheng
    Weizhi Yu
    Guojiao Wu
    Rui Zhang
    Wen-Dao Chu
    Yan Zhang
    Jianbo Wang
    [J]. Nature Chemistry, 2017, 9 : 970 - 976
  • [8] Lending a hand to asymmetric trifluoromethylthiolation: enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides
    Guoliang Mao
    Lei Chen
    Congyang Wang
    [J]. Science China Chemistry, 2017, 60 : 1565 - 1566
  • [9] RING EXPANSION OF 2-ETHYNYLTHIACYCLOALKANES VIA SULFONIUM YLIDES BY [2,3]-SIGMATROPIC REARRANGEMENT
    SASHIDA, H
    TSUCHIYA, T
    [J]. HETEROCYCLES, 1982, 19 (11) : 2147 - 2150
  • [10] 2,3-sigmatropic rearrangement of sulfonium ylides generated by addition of samarium carbenoids
    Kunishima, M
    Nakata, D
    Goto, C
    Hioki, K
    Tani, S
    [J]. SYNLETT, 1998, (12) : 1366 - 1368
12345