Organocatalytic route to the enantioselective synthesis of syn/ anti-α-hydrazino-γ-fluoro alcohols

被引：0
|
作者：
Khonde, Nilesh S. [1 ,2 ]
Said, Madhukar S. [1 ,2 ]
Danve, Shivam S. [1 ]
Kumar, Pradeep [1 ,2 ]
机构：
[1] CSIR Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
TETRAHEDRON LETTERS | 2024年 / 145卷
关键词：
Organocatalyst; HWE olefination; alpha-Fluorination; alpha-Amination; Enantioselectivity; Diastereoselectivity; CATALYZED ASYMMETRIC AMINATION; ISOSTERES; ALDEHYDES;
D O I：
10.1016/j.tetlet.2024.155179
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general organocatalytic method has been developed for the asymmetric synthesis of alpha-hydrazino-gamma-fluoro alcohols, a precursor to syn/anti-1,3-fluoro amines. The strategy employs alpha-fluorination catalyzed by prolinederived catalyst, (S)-alpha,alpha-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether followed by Horner-Wadsworth-Emmons (HWE) olefination of aldehydes, and proline-catalyzed alpha-amination as the key steps. The title compounds showed excellent diastereoselectivity (up to 99:1) and enantioselectivity (up to 99 %).
引用
收藏
页数：4
相关论文
共 50 条
  • [1] Catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols
    Kobayashi, S
    Ishitani, H
    Ueno, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) : 431 - 432
  • [2] Enantioselective Synthesis of anti- and syn-Homopropargyl Alcohols via Chiral Bronsted Acid Catalyzed Asymmetric Allenylboration Reactions
    Chen, Ming
    Roush, William R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) : 10947 - 10952
  • [3] A stereocontrolled synthetic route to anti-β-amino alcohols
    Kang, SH
    Hwang, YS
    Youn, JH
    TETRAHEDRON LETTERS, 2001, 42 (43) : 7599 - 7603
  • [4] Organocatalytic enantioselective synthesis of α-fluoro-β-amino acid derivatives
    Straub, Matthew
    Birman, Vladimir
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [5] Organocatalytic Enantioselective Synthesis of α-Fluoro-β-amino Acid Derivatives
    Straub, Matthew R.
    Birman, Vladimir B.
    ORGANIC LETTERS, 2018, 20 (23) : 7550 - 7553
  • [6] Organocatalytic anti-Selective Mannich Reactions with Fluorinated Aldimines: Synthesis of anti-γ-Fluoroalkyl-γ-amino Alcohols
    Fustero, Santos
    Mojarrad, Fatemeh
    Perez Carrion, Maria Dolores
    Sanz-Cervera, Juan F.
    Acena, Jose Luis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (30) : 5208 - 5214
  • [7] Enantioselective Synthesis of β-Hydrazino Alcohols Using Alcohols and N-Boc-Hydrazine as Substrates
    Cui, Zhihao
    Du, Da-Ming
    ORGANIC LETTERS, 2016, 18 (21) : 5616 - 5619
  • [8] Asymmetric aminolysis of aromatic epoxides:: A facile catalytic enantioselective synthesis of anti-β-amino alcohols
    Bartoli, G
    Bosco, M
    Carlone, A
    Locatelli, M
    Massaccesi, M
    Melchiorre, P
    Sambri, L
    ORGANIC LETTERS, 2004, 6 (13) : 2173 - 2176
  • [9] Organocatalytic Enantioselective Synthesis of Chiral Diarylmethylamines from Racemic Alcohols
    Chen, Min
    Han, Yaodong
    Ma, Dengke
    Wang, Yong
    Lai, Zengwei
    Sun, Jianwei
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (07) : 587 - 593
  • [10] Enantioselective Synthesis of anti- and syn-Homopropargyl Alcohols via Chiral Bronsted Acid Catalyzed Asymmetric Allenylboration Reactions (vol 134, 10947, 2012)
    Chen, Ming
    Roush, William R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 12320 - 12320
12345