Enantioselective radical addition reactions to imines using binaphthol-derived chiral N-triflyl phosphoramides

被引:43
|
作者
Lee, Sunggi [1 ]
Kim, Sunggak [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Sch Mol Sci BK 21, Dept Chem, Taejon 305701, South Korea
关键词
Radical; Chiral Bronsted acid; Imine; Asymmetric; Catalytic; BRONSTED ACID CATALYST; TRANSFER HYDROGENATION; ALKYLATION; INDOLES;
D O I
10.1016/j.tetlet.2009.02.136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Binaphthol-derived chiral phosphoric acid catalysts were applied to enantioselective radical addition reactions of imines and provided chiral amines with good enantioselectivities (73-84% ee). Furthermore,, the enantioselectivities were not affected by either electronic properties of phenyl imines or radical precursors. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3345 / 3348
页数:4
相关论文
共 50 条
  • [21] Asymmetric sequential Michael addition-N-heterocyclization reactions involving chiral imines
    dAngelo, J
    Cave, C
    Desmaele, D
    ISRAEL JOURNAL OF CHEMISTRY, 1997, 37 (01) : 81 - 85
  • [22] Catalytic enantioselective decarboxylative nucleophilic addition reactions using chiral organocatalysts
    Hyodo, Kengo
    Nakamura, Shuichi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2781 - 2792
  • [23] The highly enantioselective addition of indoles to N-acyl imines with use of a chiral phosphoric acid catalyst
    Rowland, Gerald B.
    Rowland, Emily B.
    Liang, Yuxue
    Perman, Jason A.
    Antilla, Jon C.
    ORGANIC LETTERS, 2007, 9 (14) : 2609 - 2611
  • [24] Enantioselective radical allylation reactions using chiral lanthanide Lewis acids
    Sibi, MP
    Manyem, S
    Subramaniam, R
    TETRAHEDRON, 2003, 59 (52) : 10575 - 10580
  • [25] Enantioselective radical addition to N-acyl hydrazones mediated by chiral Lewis acids
    Friestad, GK
    Shen, YH
    Ruggles, EL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) : 5061 - 5063
  • [26] Enantioselective radical addition reactions to the C=N bond utilizing chiral quaternary ammonium salts of hypophosphorous acid in aqueous media
    Cho, Dae Hyan
    Jang, Doo Ok
    CHEMICAL COMMUNICATIONS, 2006, (48) : 5045 - 5047
  • [27] Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines
    Hou, Ya-Jing
    Wang, Yang-Ling
    Chang, Junbiao
    Chai, Guo-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13137 - 13149
  • [28] Highly enantioselective 1,4-addition of diorganozinc reagents to cyclic enones using chiral diphosphite ligands derived from H8-binaphthol
    Liang, L
    Au-Yeung, TTL
    Chan, ASC
    ORGANIC LETTERS, 2002, 4 (22) : 3799 - 3801
  • [29] Enantioselective diethylzinc addition to aldehydes using azetidine-derived chiral catalysts
    Hermsen, PJ
    Cremers, JGO
    Thijs, L
    Zwanenburg, B
    TETRAHEDRON LETTERS, 2001, 42 (25) : 4243 - 4245
  • [30] Enantioselective hydrophosphonylation of N-Boc imines using chiral guanidine-thiourea catalysts
    Chassillan, Louis
    Yamashita, Yasuhiro
    Yoo, Woo-Jin
    Toffano, Martial
    Guillot, Regis
    Kobayashi, Shu
    Vo-Thanh, Giang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10560 - 10564