Exceptionally mild, high-yield synthesis of α-fluoro acrylates

被引：57
|
作者：
Zajc, Barbara [1 ]
Kake, Shivani [1 ]
机构：
[1] CUNY City Coll, Dept Chem, New York, NY 10031 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 20期
关键词：
WADSWORTH-EMMONS REACTION; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALPHA-FLUORO-ALPHA; BETA-UNSATURATED ESTERS; CARBONYL-COMPOUNDS; ALPHA; (Z)-ALPHA-FLUORO-ALPHA; REDUCTION-OLEFINATION; VERSATILE REAGENT; ORGANIC-COMPOUNDS;
D O I：
10.1021/ol0616236
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel achiral and chiral alkyl alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol- 2-ylsulfonyl) acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 degrees C or at room temperature giving high yields of alpha-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of alpha-(1,3-benzothiazol-2-ylsulfonyl)-rfluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)(2)P(O)CHFCOOEt has also been compared.
引用
收藏
页码：4457 / 4460
页数：4
相关论文
共 50 条
  • [41] High-yield synthesis of superhydrophilic polypyrrole nanowire networks
    Zhong, WB
    Liu, SM
    Chen, XH
    Wang, YX
    Yang, WT
    MACROMOLECULES, 2006, 39 (09) : 3224 - 3230
  • [42] A High-Yield and Cost-Effective Synthesis of Spirotetramat
    Guiqing Xu
    Jiahao Wang
    Yingjie Zhou
    Longfei Mao
    Russian Journal of Organic Chemistry, 2020, 56 : 1775 - 1778
  • [43] High-yield chemical synthesis by reprogramming central metabolism
    Yu, Vivian Y.
    Chang, Michelle C. Y.
    NATURE BIOTECHNOLOGY, 2016, 34 (11) : 1128 - 1129
  • [44] A High-Yield and Cost-Effective Synthesis of Spirotetramat
    Xu, Guiqing
    Wang, Jiahao
    Zhou, Yingjie
    Mao, Longfei
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (10) : 1775 - 1778
  • [45] High-yield synthesis of the first arachno-silaborane
    Wesemann, L
    Ganter, B
    ORGANOMETALLICS, 1996, 15 (10) : 2569 - 2570
  • [46] A HIGH-YIELD ONE-STEP SYNTHESIS OF HYDROXYLAMINES
    MURRAY, RW
    SINGH, M
    SYNTHETIC COMMUNICATIONS, 1989, 19 (20) : 3509 - 3522
  • [47] HIGH-YIELD SYNTHESIS OF PROPANAL FROM METHANE AND AIR
    GREEN, MLH
    TSANG, SC
    VERNON, PDF
    YORK, APE
    CATALYSIS LETTERS, 1992, 13 (04) : 341 - 347
  • [48] A facile high-yield synthesis and purification of tetrabutylammonium tetrabutylborate
    Hoff, RH
    Hengge, AC
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01): : 195 - 195
  • [49] HIGH-YIELD SYNTHESIS OF LANTHANOFULLERENES VIA LANTHANUM CARBIDE
    BANDOW, S
    SHINOHARA, H
    SAITO, Y
    OHKOHCHI, M
    ANDO, Y
    JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (23): : 6101 - 6103
  • [50] High-yield synthesis and optical response of gold nanostars
    Senthil Kumar, Pandian
    Pastoriza-Santos, Isabel
    Rodriguez-Gonzalez, Benito
    Garcia de Abajo, F. Javier
    Liz-Marzan, Luis M.
    NANOTECHNOLOGY, 2008, 19 (01)
12345