Enantioselective Allylic Substitution of Morita-Baylis-Hillman Adducts Catalyzed by Chiral Bifunctional Ferrocenylphosphines

被引:22
|
作者
Zhu, Linglong [1 ]
Hu, Haiwen [1 ]
Qi, Liang [1 ]
Zheng, Yi [1 ]
Zhong, Weihui [1 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Collaborat Innovat Ctr Green Pharmaceut Engn, Chao Wang Rd 18th, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
Asymmetric catalysis; Amination; Phosphanes; Configuration determination; N-SULFONATED IMINES; INDOLE-DERIVATIVES; KINETIC RESOLUTION; ACTIVATED OLEFINS; HILIMAN REACTION; MBH-CARBONATES; ACETATES; ALKYLATION; AMINATION; ORGANOCATALYSTS;
D O I
10.1002/ejoc.201600045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of air-stable chiral ferrocenylphosphines (LB1-LB4) were prepared and used in the asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) adducts with phthalimide under mild reaction conditions; the (R,S-Fc)-ferrocenylphosphine LB4 afforded the desired amination products 3 in moderate yields with excellent enantioselectivities. The absolute configuration of 3o was confirmed by X-ray analysis.
引用
收藏
页码:2139 / 2144
页数:6
相关论文
共 50 条
  • [41] Asymmetric organocatalytic Morita-Baylis-Hillman reaction and asymmetric organocatalytic transformations of Morita-Baylis-Hillman adducts. An update
    Pellissier, Helene
    TETRAHEDRON, 2025, 172
  • [42] Biological Activities of Morita-Baylis-Hillman Adducts (MBHA)
    Ferreira, Larissa Adilis Maria Paiva
    de Lima, Louise Mangueira
    Ferreira, Laercia Karla Diega Paiva
    Bernardo, Larissa Rodrigues
    Castro, Aleff
    Lima Jr, Claudio Gabriel
    de Almeida Vasconcellos, Mario Luiz Araujo
    Piuvezam, Marcia Regina
    MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2023, 23 (17) : 1691 - 1710
  • [43] An-PIQ Catalyzed Kinetic Resolution of β-lodo Morita-Baylis-Hillman Adducts
    Zhu, Mingyu
    Deng, Weiping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (10) : 2397 - 2406
  • [44] Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
    Mansilla, Javier
    Saa, Jose M.
    MOLECULES, 2010, 15 (02): : 709 - 734
  • [45] Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts
    Qi, Jifeng
    Zheng, Jing
    Cui, Sunliang
    ORGANIC LETTERS, 2018, 20 (05) : 1355 - 1358
  • [46] Organocatalyzed Regio- and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent
    Furukawa, Tatsuya
    Nishimine, Takayuki
    Tokunaga, Etsuko
    Hasegawa, Kimiko
    Shiro, Motoo
    Shibata, Norio
    ORGANIC LETTERS, 2011, 13 (15) : 3972 - 3975
  • [47] Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates Catalysed by Modified Cinchona Alkaloids
    Zhang, Shan-Jun
    Cui, Hai-Lei
    Jiang, Kun
    Li, Rui
    Ding, Zhen-Yu
    Chen, Ying-Chun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (33) : 5804 - 5809
  • [48] Amino acid-peptide-catalyzed enantioselective Morita-Baylis-Hillman reactions
    Vasbinder, Melissa M.
    Imbriglio, Jason E.
    Miller, Scott J.
    TETRAHEDRON, 2006, 62 (49) : 11450 - 11459
  • [49] Catalytic Enantioselective Transannular Morita-Baylis-Hillman Reaction
    Mato, Raquel
    Manzano, Ruben
    Reyes, Efraim
    Carrillo, Luisa
    Uria, Uxue
    Vicario, Jose L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) : 9495 - 9499
  • [50] 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