Diastereoselective amination of vinylic sulfoximines:: application to the asymmetric synthesis of functionalized β-substituted and β,β-disubstituted β-amino acids, and of γ-amino alcohols

被引:14
|
作者
Gais, HJ [1 ]
Loo, R [1 ]
Das, P [1 ]
Raabe, G [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
D O I
10.1016/S0040-4039(00)00307-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric synthesis of protected beta-substituted and beta,beta-disubstituted beta-amino acids, which carry a hydroxyalkyl side chain, from sulfonimidoyl functionalized homoallylic alcohols is described. The method allows for an asymmetric synthesis of amino alcohols as well. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2851 / 2854
页数:4
相关论文
共 50 条
  • [31] Stereoselective synthesis of beta-amino alcohols: diastereoselective reduction of chiral alpha'-amino enones derived from amino acids
    Chung, SK
    Kang, DN
    TETRAHEDRON-ASYMMETRY, 1997, 8 (18) : 3027 - 3030
  • [32] Asymmetric synthesis of α,β-substituted γ-amino acids via conjugate addition
    Sabala, Rocio
    Assad, Salomon
    Mendoza, Angel
    Jimenez, Jacqueline
    Sansinenea, Estibaliz
    Ortiz, Aurelio
    TETRAHEDRON LETTERS, 2019, 60 (26) : 1741 - 1744
  • [33] Asymmetric synthesis of β-heterocycle substituted L-α-amino acids
    Saghiyan, AS
    Geolchanyan, AV
    Petrosyan, SG
    Ghochikyan, TV
    Haroutunyan, VS
    Avetisyan, AA
    Belokon, YN
    Fisher, K
    TETRAHEDRON-ASYMMETRY, 2004, 15 (04) : 705 - 711
  • [34] Application of sharpless asymmetric dihydroxylation to synthesis of chiral β-amino alcohols
    Liu, WM
    Liu, XY
    Song, RJ
    Zhang, SY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (03) : 341 - 345
  • [35] Enantio- and diastereoselective construction of α,α-disubstituted α-amino acids for the synthesis of biologically active compounds
    Ohfune, Y
    Shinada, T
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) : 5127 - 5143
  • [36] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids
    Cardillo, G
    Tomasini, C
    CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) : 117 - &
  • [37] Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids
    Perveen, Shahida
    Rahman, Tahir
    Ali, Tariq
    Wang, Lingyun
    Zhang, Junjie
    Khan, Ajmal
    ADVANCED SCIENCE, 2025,
  • [38] Application of metal reagent to the asymmetric synthesis of α,α-amino acids
    Hu, AG
    Zhang, LY
    Wang, SW
    Wang, JT
    SYNTHETIC COMMUNICATIONS, 2002, 32 (14) : 2143 - 2147
  • [39] Asymmetric Synthesis of α-Aryl Amino Acids; Aryne-Mediated Diastereoselective Arylation
    Jones, Elizabeth P.
    Jones, Peter
    Barrett, Anthony G. M.
    ORGANIC LETTERS, 2011, 13 (05) : 1012 - 1015
  • [40] Synthesis of enantiopure cyclobutane amino acids and amino alcohols
    Balo, C
    Caamaño, O
    Fernández, F
    López, C
    TETRAHEDRON-ASYMMETRY, 2005, 16 (15) : 2593 - 2597