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
  • [31] One-pot synthesis of glycoconjugates
    Morrison, Justin T.
    Lewallen, Daniel M.
    Iyer, Suri S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [32] A ONE-POT SYNTHESIS OF FLAVONES
    FOZDAR, BI
    KHAN, SA
    SHAMSUDDIN, KM
    CHEMISTRY & INDUSTRY, 1986, (17) : 586 - 586
  • [33] ONE-POT SYNTHESIS OF RUFLOXACIN
    CECCHETTI, V
    FRAVOLINI, A
    SCHIAFFELLA, F
    SYNTHETIC COMMUNICATIONS, 1991, 21 (22) : 2301 - 2308
  • [34] Rapid one-pot synthesis of functionalized 2,3-dihydrobenzofurans.
    Kuethe, JT
    Wong, A
    Journet, M
    Davies, IW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U330 - U330
  • [35] Synthesis of siloxy- and alkoxy-substituted ZnO-aggregates for CVS of ZnO
    Schoenen, R
    Merz, K
    Rell, S
    Driess, M
    JOURNAL DE PHYSIQUE IV, 2001, 11 (PR3): : 547 - 551
  • [36] Rapid one-pot microwave-assisted synthesis of a hexadentate chelating agent
    Kane, CT
    Vadapalli, SR
    Hossain, T
    SYNLETT, 2005, (02) : 283 - 284
  • [37] Crystal Structures of Two Compounds from a Rapid and One-pot Synthesis Method
    周宝晗
    徐保明
    严伯承
    马丽
    陈坤
    华云涛
    结构化学, 2017, 36 (03) : 409 - 415
  • [38] Rapid and one-pot synthesis of tri- to tetradeca-deutero nicotines
    Gouthami, Pashikanti
    Goud, Gadela Karteek
    Mainkar, Prathama S.
    Chandrasekhar, Srivari
    TETRAHEDRON LETTERS, 2020, 61 (13)
  • [39] Crystal Structures of Two Compounds from a Rapid and One-pot Synthesis Method
    Zhou Bao-Han
    Xu Bao-Ming
    Yan Bo-Cheng
    Ma Li
    Chen Kun
    Hua Yun-Tao
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2017, 36 (03) : 409 - 415
  • [40] One-pot synthesis of dendritic polyamide
    Yamakawa, Y
    Ueda, M
    Takeuchi, K
    Asai, M
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1999, 37 (18) : 3638 - 3645
12345