Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling

被引：50
|
作者：
Gustafson, Jeffrey L. [1 ]
Lim, Daniel [1 ]
Barrett, Kimberly T. [1 ]
Miller, Scott J. [1 ]
机构：
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 22期
基金：
美国国家卫生研究院;
关键词：
atropisomerism; bromination; cross-coupling reactions; peptides; regioselectivity; AXIALLY CHIRAL BIARYLS; ASYMMETRIC-SYNTHESIS; HALOGENATED NITROGEN; METAL-COMPLEXES; OXYGEN; SCOPE;
D O I：
10.1002/anie.201101147
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A selective sequence: An enantioselective synthesis (see scheme) of atropisomerically defined p-terphenyls, as well as tetra- and pentaaryl compounds is reported. The synthesis proceeds through sequential atropisomer-selective electrophilic aromatic substitution and regioselective palladium-catalyzed cross-coupling reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5125 / 5129
页数：5
相关论文
共 50 条
  • [31] Synthesis of biaryl cyclic peptides through solid-phase borylation and cyclization by a Suzuki-Miyaura cross-coupling
    Afonso, A.
    Feliu, L.
    Planas, M.
    JOURNAL OF PEPTIDE SCIENCE, 2010, 16 : 48 - 48
  • [32] Synthesis of Well-Defined Head-to-Tail-Type Oligothiophenes by Regioselective Deprotonation of 3-Substituted Thiophenes and Nickel-Catalyzed Cross-Coupling Reaction
    Tanaka, Shota
    Tamba, Shunsuke
    Tanaka, Daiki
    Sugie, Atsushi
    Mori, Atsunori
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) : 16734 - 16737
  • [33] The synthesis of novel highly substituted benzene derivatives for use in palladium-catalysed cross-coupling reactions
    Hird, M
    Lewis, RA
    Toyne, KJ
    West, JJ
    Wilson, MK
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20): : 3479 - 3484
  • [34] Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions (vol 59, pg 4835, 2020)
    Ben-Lulu, M.
    Gaster, E.
    Libman, A.
    Pappo, D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (35) : 14722 - 14722
  • [35] Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction
    Xu, Si-Yu
    Zhang, Rui
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (20) : 4492 - 4496
  • [36] Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes
    Matsuhashi, H
    Hatanaka, Y
    Kuroboshi, M
    Hiyama, T
    HETEROCYCLES, 1996, 42 (01) : 375 - 384
  • [37] Solution-phase synthesis of an aminomethyl-substituted biaryl library via sequential amine N-alkylation and Suzuki cross-coupling
    Organ, MG
    Arvanitis, EA
    Dixon, CE
    Lavorato, DJ
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (05): : 473 - 476
  • [38] Solid-phase synthesis of aryl-substituted thienoindolizines: Sequential Pictet-Spengler, bromination and Suzuki cross-coupling reactions of thiophenes
    Le Quement, Sebastian T.
    Nielsen, Thomas E.
    Meldal, Morten
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (03): : 447 - 455
  • [39] Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties
    Chang, Ning-hui
    Chen, Xi-chao
    Nonobe, Hikaru
    Okuda, Yasuhiro
    Mori, Hiroki
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    ORGANIC LETTERS, 2013, 15 (14) : 3558 - 3561
  • [40] Regioselective bromination and subsequent Suzuki cross-coupling of highly electron deficient 5,10,15,20-tetrakis(trifluoromethyl)porphyrin (vol 56, pg 7779, 2000)
    Tse, MK
    Zhou, ZY
    Mak, TCW
    Chan, KS
    TETRAHEDRON, 2000, 56 (47) : 9399 - 9399
12345