Synthesis of Optically Active α-Trifluoromethylamines by Rearrangement of β-Amino-α-trifluoromethyl Alcohols

被引：8
|
作者：
Neouchy, Zeina [1 ]
Pardo, Domingo Gomez [1 ]
Cossy, Janine [1 ]
机构：
[1] PSL Univ, CNRS, ESPCI Paris, Lab Chim Organ,Inst Chem Biol & Innovat CBI, 10 Rue Vauquelin, F-75231 Paris 05, France
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 19期
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC TRIFLUOROMETHYLATION; RING EXPANSION; SUBSTITUTED; 3-FLUOROPIPERIDINES; STEREOSPECIFIC REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; PROLINOLS; CONTRACTION; ENLARGEMENT; REAGENTS;
D O I：
10.1021/acs.orglett.8b02353
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of various optically active alpha-trifluoromethylamines has been realized from beta-amino-alpha-trifluoromethyl alcohols via an aziridinium ion intermediate under kinetic conditions.
引用
收藏
页码：6017 / 6021
页数：5
相关论文
共 50 条
  • [21] Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines
    Carroccia, Laura
    Fioravanti, Stefania
    Pellacani, Lucio
    Sadun, Claudia
    Tardella, Paolo A.
    TETRAHEDRON, 2011, 67 (30) : 5375 - 5381
  • [22] SYNTHESIS OF OPTICALLY-ACTIVE ALLYLIC ALCOHOLS
    KANG, SK
    KIM, SG
    CHO, DG
    JEON, JH
    SYNTHETIC COMMUNICATIONS, 1993, 23 (05) : 681 - 684
  • [23] Biocatalytic synthesis of optically active tertiary alcohols
    Kourist, Robert
    Bornscheuer, Uwe T.
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2011, 91 (03) : 505 - 517
  • [24] Biocatalytic synthesis of optically active tertiary alcohols
    Robert Kourist
    Uwe T. Bornscheuer
    Applied Microbiology and Biotechnology, 2011, 91 : 505 - 517
  • [25] Molecular structures of β-amino-α-bromovinyl trifluoromethyl ketones
    S. V. Fedorov
    A. Yu. Rulev
    N. N. Chipanina
    A. M. Shulunova
    V. G. Nenajdenko
    E. S. Balenkova
    D. A. Tyurin
    V. K. Turchaninov
    Russian Chemical Bulletin, 2005, 54 : 103 - 107
  • [26] Synthesis of α-Quaternary Aldehydes via a Stereoselective Semi-Pinacol Rearrangement of Optically Active Epoxy Alcohols
    Hirama, Naomichi
    Sakamoto, Ryu
    Maruoka, Keiji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1390 - 1393
  • [27] Molecular structures of β-amino-α-bromovinyl trifluoromethyl ketones
    Fedorov, SV
    Rulev, AY
    Chipanina, NN
    Shulunova, AM
    Nenajdenko, VG
    Balenkova, ES
    Tyurin, DA
    Turchaninova, VK
    RUSSIAN CHEMICAL BULLETIN, 2005, 54 (01) : 103 - 107
  • [28] Synthesis of a heptapeptide containing an optically active trifluoromethyl-λ6-tetrafluorosulfanyl-substituted amino acid
    Ikeda, Akari
    Capellan, Aimee
    Welch, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [29] STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS
    REETZ, MT
    DREWES, MW
    SCHMITZ, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1141 - 1143
  • [30] Bioreactor systems for the production of optically active amino acids and alcohols
    Nanba, Hirokazu
    Yasohara, Yoshihiko
    Hasegawa, Junzo
    Takahashi, Satomi
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 503 - 508
12345