Direct carbon-carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters

被引:12
|
作者
Yost, Julianne M. [1 ]
Alfie, Rachel J. [1 ]
Tarsis, Emily M. [1 ]
Chong, Insun [1 ]
Coltart, Don M. [1 ]
机构
[1] Duke Univ, Dept Chem, Durham, NC 27706 USA
基金
美国国家科学基金会;
关键词
DARZENS; ACIDS; TRIETHYLAMINE; 1,3-DIKETONES; CONDENSATION; KETONES; FACILE; ESTERS;
D O I
10.1039/c0cc02345k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr(2)center dot OEt(2) and i-Pr(2)NEt to produce alpha-halo-beta-hydroxy thioesters.
引用
收藏
页码:571 / 572
页数:2
相关论文
共 50 条
  • [1] Direct carbon-carbon bond formation via soft enolization of thioesters
    Coltart, Don M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [2] Direct Carbon-Carbon Bond Formation via Soft Enolization of Thioesters: An Operationally Simple Mannich Addition Reaction
    Yost, Julianne M.
    Garnsey, Michelle R.
    Kohler, Mark C.
    Coltart, Don M.
    SYNTHESIS-STUTTGART, 2009, (01): : 56 - 58
  • [3] Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes
    Sauer, Scott J.
    Garnsey, Michelle R.
    Coltart, Don M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) : 13997 - 13999
  • [4] ORGN 666-Direct carbon-carbon bond formation via chemoselective soft enolization of thioesters
    Zhou, Guoqiang
    Coltart, Don M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [5] Direct carbon-carbon bond formation via reductive soft enolization: a syn-selective Mannich addition of α-iodo thioesters
    Ngoc Truong
    Sauer, Scott J.
    Seraphin-Hatcher, Cyndie
    Coltart, Don M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (33) : 7864 - 7868
  • [6] Direct Carbon-Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters
    Kohler, Mark C.
    Yost, Julianne M.
    Garnsey, Michelle R.
    Coltart, Don M.
    ORGANIC LETTERS, 2010, 12 (15) : 3376 - 3379
  • [7] ORGN 142-Facile and efficient direct aldol addition of α-halogenated thioesters via soft enolization
    Yost, Julianne M.
    Coltart, Don M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [8] A kinetically controlled direct aldol addition of α-chloro thioesters via soft enolization
    Alfie, Rachel J.
    Ngoc Truong
    Yost, Julianne M.
    Coltart, Don M.
    TETRAHEDRON LETTERS, 2017, 58 (03) : 185 - 189
  • [9] A direct aldol addition of simple thioesters employing soft enolization
    Zhou, Guoqiang
    Yost, Julianne M.
    Coltart, Don M.
    SYNTHESIS-STUTTGART, 2007, 3 (03): : 478 - 482
  • [10] Direct carbon-carbon bond formation via soft enolization: A facile and efficient synthesis of 1,3-diketones
    Lim, Daniel
    Fang, Fang
    Zhou, Guoqiang
    Coltart, Don M.
    ORGANIC LETTERS, 2007, 9 (21) : 4139 - 4142