Practical asymmetric synthesis of trifluoromethyl-containing aminoester using a modified Davis protocol

被引：5
作者：
Alimardanov, Asaf [1 ]
Schmid, Jean [1 ]
Afragola, Jay [1 ]
Khafizova, Gulnaz [1 ]
机构：
[1] Wyeth Res, Pearl River, NY 10965 USA
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2008年 / 12卷 / 03期
关键词：
D O I：
10.1021/op700259d
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Practical synthesis of aminoester 1 starting from 1,1,1-trifluoro-3-iodopropane is presented. Use of Ti(Oi-Pr)(4) as a Lewis acid for condensation of intermediate aldehyde 8 with (S)-(+)-p-toluene-sulfinamide was found to be critical. Conditions for a reproducible and high-yielding Wittig reaction of aldehyde hydrate with phosphorus ylide 4, that appear to have general applicability, are described.
引用
收藏
页码：424 / 428
页数：5
相关论文
共 50 条
  • [31] Aminoazoles in heterocycles synthesis: II. Trifluoromethyl-containing diketones in the synthesis of pyrazolo[1,5-a]pyrimidines
    Emelina, EE
    Petrov, AA
    Firsov, AV
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (06) : 852 - 858
  • [32] Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids
    Luis Acena, Jose
    Sorochinsky, Alexander E.
    Soloshonok, Vadim A.
    SYNTHESIS-STUTTGART, 2012, 44 (11): : 1591 - 1602
  • [33] Asymmetric Synthesis of Chiral Trifluoromethyl Containing Heterocyclic Amino Acids
    Zhao, Liang
    Zhou, Shengbin
    Tong, Junhua
    Wang, Jiang
    Liu, Hong
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (10) : 1540 - 1548
  • [34] Trifluoromethyl-containing 1,2,4-triazines. Synthesis on the base of perfluorobiacetyl and reactions with thiosemicarbazide and thiourea
    Saloutina, L. V.
    Zapevalov, A. Ya.
    Kodess, M. I.
    Slepukhin, P. A.
    Ganebnykh, I. N.
    Saloutin, V. I.
    Chupakhin, O. N.
    JOURNAL OF FLUORINE CHEMISTRY, 2019, 227
  • [35] N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl-Containing Amines and Amino Acids of Pharmaceutical Importance
    Mei, Haibo
    Xie, Chen
    Han, Jianlin
    Soloshonok, Vadim A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (36) : 5917 - 5932
  • [36] Asymmetric synthesis of isoxazole and trifluoromethyl-containing 3,2′-pyrrolidinyl dispirooxindoles via squaramide-catalysed [3+2] cycloaddition reactions
    Li, Tong-Hao
    Du, Da-Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (04) : 817 - 823
  • [37] Synthesis, Insecticidal Activity, and Structure-Activity Relationship of Trifluoromethyl-Containing Phthalic Acid Diamide Structures
    Feng, Mei-Li
    Li, Yu-Feng
    Zhu, Hong-Jun
    Zha, Liang
    Xi, Bin-Bin
    Ni, Jue-Ping
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (20) : 10999 - 11006
  • [38] Synthesis of trifluoromethyl-containing isoindolinones from tertiary enamides via a cascade radical addition and cyclization process
    Yu, Hui
    Jiao, Mingdong
    Fang, Xiaowei
    Xuan, Pengfei
    RSC ADVANCES, 2018, 8 (42): : 23919 - 23923
  • [39] Convergent procedure for the synthesis of trifluoromethyl-containing N-(pyridinyl-triazolyl)pyrimidin-2-amines
    Bonacorso, Helio G.
    Bortolotto, Guilherme P.
    Navarini, Jussara
    Porte, Liliane M. F.
    Wiethan, Carson W.
    Zanatta, Nilo
    Martins, Marcos A. P.
    Flores, Alex F. C.
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (12) : 1297 - 1301
  • [40] 1,2-Addition to trifluoromethylated β-enamino diketones: regioselective synthesis of trifluoromethyl-containing azomethine pyrazoles and isoxazoles
    Pianoski, Karlos Eduardo
    Poletto, Julia
    Vieira da Silva, Michael Jackson
    Ascencio Camargo, Jeniffer Nascimento
    Jacomini, Andrey Petita
    Goncalves, Davana Silva
    Back, Davi Fernando
    Moura, Sidnei
    Rosa, Fernanda Andreia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (13) : 2524 - 2537
12345