Silicon-Directed Rhenium-Catalyzed Allylic Carbaminations and Oxidative Fragmentations of γ-Silyl Allylic Alcohols

被引：12
作者：
Chavhan, Sanjay W. [1 ]
Cook, Matthew J. [1 ]
机构：
[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 17期
关键词：
allylic substitution; carbamination; Hiyama coupling; rhenium; silicon; ELECTRON-DEFICIENT AMINES; ENANTIOSELECTIVE REDUCTION; PROPARGYLIC ALCOHOLS; AMINATION; ISOMERIZATION; SUBSTITUTION; IMINES; REARRANGEMENT; VERSATILE; ALLYLATION;
D O I：
10.1002/chem.201400104
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly regioselective allylic substitution of -silyl allylic alcohols has been achieved that provides the branched isomer as a single product. This high level of regiocontrol is achieved through the use of a vinyl silane group that can perform a Hiyama coupling providing 1,3-disubstituted allylic amines. An unusual oxidative fragmentation product was also observed at elevated temperature that appears to proceed by a Fleming-Tamao-type oxidation-elimination pathway.
引用
收藏
页码：4891 / 4895
页数：5
相关论文
共 70 条
  • [1] [Anonymous], 1997, ANGEW CHEM INT ED EN, V36, P976
  • [2] [Anonymous], 1968, ANGEW CHEM INT ED EN, V7, P295
  • [3] [Anonymous], 2012, ANGEW CHEM INT ED, V51, P3470
  • [4] [Anonymous], 2009, ANGEW CHEM INT ED, V48, P4426
  • [5] BAILEY N, 1960, J CHEM SOC, V290
  • [6] Bartels B., 2002, EUR J INORG CHEM, P2569
  • [7] Allylic Substitutions Catalyzed by Miscellaneous Metals
    Begouin, Jeanne-Marie
    Klein, Johannes E. M. N.
    Weickmann, Daniel
    Plietker, Bernd
    [J]. TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 : 269 - 320
  • [8] Molybdenum-catalyzed asymmetric allylic alkylations
    Belda, O
    Moberg, C
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (03) : 159 - 167
  • [9] Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes
    Bellemin-Laponnaz, S
    Le Ny, JP
    Osborn, JA
    [J]. TETRAHEDRON LETTERS, 2000, 41 (10) : 1549 - 1552
  • [10] Bellemin-Laponnaz S., 1997, ANGEW CHEM, V109, P1011
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