Organocatalytic regio- and enantioselective vinylogous aza-Morita-Baylis-Hillman reaction

被引：2
|
作者：
Gondo, Naruhiro [1 ]
Fujimura, Koki [1 ]
Hyakutake, Ryuichi [1 ]
Ueda, Yoshihiro [1 ]
Kawabata, Takeo [1 ,2 ]
机构：
[1] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan
[2] Int Univ Hlth & Welf, Dept Pharmaceut Sci, 137-1 Enokizu, Okawa, Fukuoka 831501, Japan
来源：
TETRAHEDRON LETTERS | 2023年 / 115卷
关键词：
Asymmetric organocatalysis; Aza-Morita-Baylis-Hillman reaction; Chiral amine; Regioselectivity; 7-Selectivity; SITE-SELECTIVE ACYLATION; CATALYSTS; ACID; FUNCTIONALIZATION; ELLAGITANNINS; ACTIVATION; MECHANISM; STRATEGY; IMINES;
D O I：
10.1016/j.tetlet.2022.154306
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric regioselective vinylogous aza-Morita-Baylis-Hillman reactions by organocatalysis were developed. The reactions of 3-vinylcyclopentenone with various aldimines in the presence of chiral pyrrolidinopyridine catalysts gave the 7-adducts in high regioselectivity and moderate enantioselectivity.(c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [1] Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
    Mansilla, Javier
    Saa, Jose M.
    MOLECULES, 2010, 15 (02): : 709 - 734
  • [2] The highly enantioselective catalytic aza-Morita-Baylis-Hillman reaction
    Hu, Fang-Le
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05): : 587 - 595
  • [3] Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction
    Matsui, K
    Takizawa, S
    Sasai, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3680 - 3681
  • [4] Recent Advances in Organocatalytic Asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman Reactions
    Wei, Yin
    Shi, Min
    CHEMICAL REVIEWS, 2013, 113 (08) : 6659 - 6690
  • [5] Expedient Organocatalytic Aza-Morita-Baylis-Hillman Reaction through Ball-Milling
    Williams, Matthew T. J.
    Morrill, Louis C.
    Browne, Duncan L.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (48) : 17876 - 17881
  • [6] Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction
    WEI Yin SHI Min State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai China
    Chinese Science Bulletin, 2010, 55 (17) : 1699 - 1711
  • [7] Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction
    Wei Yin
    Shi Min
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1699 - 1711
  • [8] Synthesis of Onychine and Formal Synthesis of Eupolauridine via the Vinylogous Aza-Morita-Baylis-Hillman Reaction
    Clary, Kristen N.
    Back, Thomas G.
    SYNLETT, 2010, (18) : 2802 - 2804
  • [9] Enantioselective Synthesis of Polycyclic Indole Derivatives Based on aza-Morita-Baylis-Hillman Reaction
    Gao, Yuning
    Xu, Qin
    Shi, Min
    ACS Catalysis, 2015, 5 (11): : 6608 - 6614
  • [10] Organocatalyzed Enantioselective Aza-Morita-Baylis-Hillman Reaction of Cyclic Ketimine with α,β-Unsaturated γ-Butyrolactam
    Wu, Xi-Xi
    He, Yonghui
    Qiao, Xiu-Xiu
    Ma, Tao
    Zou, Chang-Peng
    Li, Ganpeng
    Zhao, Xiao-Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 6599 - 6610
12345