Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes

被引：59
|
作者：
Saadi, Jakub [1 ]
Akakura, Matsujiro [2 ]
Yamamoto, Hisashi [1 ]
机构：
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
[2] Aichi Univ Educ, Dept Chem, Kariya, Aichi 4488542, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 36期
关键词：
HETEROATOM-SUBSTITUTED ALDEHYDES; SUPER SILYL GROUP; BRONSTED ACID CATALYST; ALDOL CASCADE REACTION; MEDICINAL CHEMISTRY; STEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE ALDOL; ASYMMETRIC INDUCTION; SEQUENTIAL REACTIONS; ENOL ETHERS;
D O I：
10.1021/ja2066169
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Mukaiyama cross-aldol reaction of alpha-fluoro-, alpha-chloro-, and alpha-bromoacetaldehyde-derived (Z)tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-beta-siloxy-alpha-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel beta,delta-bissiloxy-alpha,gamma-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.
引用
收藏
页码：14248 / 14251
页数：4
相关论文
共 50 条
  • [21] One-Pot Synthesis of Thiocarbamates
    Waibel, Kevin A.
    Barther, Dennis
    Malliaridou, Triantafillia
    Moatsou, Dafni
    Meier, Michael A. R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (31) : 4508 - 4516
  • [22] Synthesis of olefins in "one-pot"
    Bellone, H
    Adamus, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U634 - U634
  • [23] ONE-POT SYNTHESIS OF SPIROGLYCOL
    Xu, Jun Ming
    Liu, Fu Sheng
    Yu, Shi Tao
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2008, 22 (01) : 149 - 152
  • [24] ONE-POT SYNTHESIS OF HEXATRIYNEDIAMINES
    FAUL, D
    LEBER, E
    HIMBERT, G
    SYNTHESIS-STUTTGART, 1987, (01): : 73 - 74
  • [25] A One-Pot Synthesis of Triazolodiazepines
    Hooyberghs, Geert
    Van Hove, Sofie
    Jacobs, Jeroen
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (21) : 4726 - 4731
  • [26] One-pot synthesis of (-)-Ambrox
    Yang, Shaoxiang
    Tian, Hongyu
    Sun, Baoguo
    Liu, Yongguo
    Hao, Yanfeng
    Lv, Yanyu
    SCIENTIFIC REPORTS, 2016, 6
  • [27] ONE-POT PROTEIN SYNTHESIS
    不详
    CHEMICAL & ENGINEERING NEWS, 2011, 89 (29) : 27 - 28
  • [28] A ONE-POT SYNTHESIS OF SULFENAMIDES
    BARTON, DHR
    HESSE, RH
    OSULLIVAN, AC
    PECHET, MM
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23): : 6702 - 6704
  • [29] One-Pot Synthesis of Spiropyrans
    Zhang, Lei
    Deng, Yawen
    Tang, Zhenyu
    Zheng, Ning
    Zhang, Chenghao
    Xie, Congxia
    Wu, Zhongtao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) : 1866 - 1869
  • [30] One-pot synthesis of carbamates
    Li, Li-Qing
    Wang, Xiao-Gang
    Guo, San-Xia
    Liu, Chong-Yang
    He, Yi-Bo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (04) : 519 - 523
12345