Chiral imines and amines based on 2-hydroxypinan-3-one

被引:0
|
作者
Ya. A. Gur’eva
O. A. Zalevskaya
L. L. Frolova
I. N. Alekseev
A. V. Kuchin
机构
[1] Institute of Chemistry,
[2] Komi Scientific Center,undefined
[3] Ural Branch,undefined
[4] Russian Academy of Sciences,undefined
[5] Syktyvkar State University,undefined
来源
关键词
chiral imines; amines; stereoisomers; stereoselectivity;
D O I
暂无
中图分类号
学科分类号
摘要
The new chiral derivatives of benzylamine and 2α-hydroxypinan-3-one (1R,2R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (2), (1S,2S,3S,5S)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (3), and (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (4) were synthesized and characterized. It was shown that reduction of the benzylimines by sodium triacetoxyborohydride formed stereoselectively 3β-substituted pinanamines.
引用
收藏
页码:920 / 923
页数:3
相关论文
共 50 条
  • [21] Highly diastereoselective radical addition to glyoxylate imines of chiral amines without additional heteroatoms
    Singh, N
    Anand, RD
    Trehan, S
    TETRAHEDRON LETTERS, 2004, 45 (14) : 2911 - 2913
  • [22] Double Stereodifferentiation in the Catalytic Asymmetric Aziridination of Imines Prepared from a-Chiral Amines
    Huang, Li
    Zhang, Yu
    Staples, Richard J.
    Huang, Rui H.
    Wulff, William D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) : 5302 - 5313
  • [23] Asymmetric Transfer Hydrogenation of Stable NH Imines for the Synthesis of Enantiopure α-Chiral Primary Amines
    Zhang, Mangang
    Li, Hui
    Wu, Keqin
    Rong, Nianxin
    Lin, Shaoquan
    Yang, Hua
    Yin, Qin
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (18) : 2211 - 2216
  • [24] ASYMMETRIC REDUCTION OF PHOSPHINYL IMINES WITH HYDRIDE REAGENTS - ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PRIMARY AMINES
    HUTCHINS, RO
    ABDELMAGID, A
    STERCHO, YP
    WAMBSGANS, A
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04): : 702 - 704
  • [25] One-Pot Synthesis of Chiral Nonracemic Amines
    Roe, Caroline
    Hobbs, Heather
    Stockman, Robert A.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22): : 9452 - 9459
  • [26] One-pot synthesis of chiral azetidines from chloroaldehyde and chiral amines
    Orr , Suvi T. M.
    Cabral, Shawn
    Fernando, Dilinie P.
    Makowski, Teresa
    TETRAHEDRON LETTERS, 2011, 52 (28) : 3618 - 3620
  • [27] DIASTEREOSELECTIVE CYCLIZATION OF 2-HYDROXYPINAN-3-ONYL AMINO ESTERS
    CALMES, M
    DAUNIS, J
    ESCALE, F
    JACQUIER, R
    ROUMESTANT, ML
    TETRAHEDRON-ASYMMETRY, 1994, 5 (09) : 1643 - 1644
  • [28] Enantioselective Pd-Catalyzed Hydrogenation of Fluorinated Imines: Facile Access to Chiral Fluorinated Amines
    Chen, Mu-Wang
    Duan, Ying
    Chen, Qing-An
    Wang, Duo-Sheng
    Yu, Chang-Bin
    Zhou, Yong-Gui
    ORGANIC LETTERS, 2010, 12 (21) : 5075 - 5077
  • [29] An approach to new chiral bicyclic imines and amines via Horner-Wadsworth-Emmons reaction
    Iwanejko, Jakub
    Sowinski, Mateusz
    Wojaczynska, Elzbieta
    Olszewski, Tomasz K.
    Gorecki, Marcin
    RSC ADVANCES, 2020, 10 (25) : 14618 - 14629
  • [30] Planar-chiral cyclopalladated ferrocenyl amines and imines as enantioselective catalysts for allylic imidate rearrangements
    Cohen, F
    Overman, LE
    TETRAHEDRON-ASYMMETRY, 1998, 9 (18) : 3213 - 3222