Catalytic Asymmetric 1,4-Reduction of α-Branched 2-Vinyl-azaarenes by a Chiral SPINOL-Derived Borophosphate

被引：15
作者：
Cao, Yang [1 ]
Zhang, Shouqi [1 ]
Antilla, Jon C. [1 ,2 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Inst Mol Design & Synth, Tianjin 300072, Peoples R China
[2] Zhejiang Sci Tech Univ, Sch Sci, Hangzhou 310018, Zhejiang, Peoples R China
来源：
ACS CATALYSIS | 2020年 / 10卷 / 19期
关键词：
phosphoryl boronate catalyst; bifunctional catalyst; chiral alkylated N-heteroarenes; asymmetric reduction; synthetic methods; ORGANOCATALYTIC TRANSFER HYDROGENATION; BRONSTED ACID; REDUCTION; ACTIVATION; ALKYLATION; COMPLEXES; DISCOVERY; KETIMINES; PYRIDINE; OLEFINS;
D O I：
10.1021/acscatal.0c02563
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The catalytic asymmetric 1,4-reduction of alpha-branched 2-vinylazaarenes by a SPINOL-derived borophosphate has been realized. A SPINOL-derived phosphoric acid is used to form a bifunctional phosphoryl boronate catalyst in situ in the presence of pinacolborane. This asymmetric 1,4-reduction reaction provides a convenient procedure to access chiral alkylated quinolines and benzothiazoles in high yields (up to 94%) and with good stereoselectivities (up to 98%).
引用
收藏
页码：10914 / 10919
页数：6
相关论文
共 60 条
  • [1] Phosphoric acid diesters as efficient catalysts for hydroaminations of nonactivated alkenes and an application to asymmetric hydroaminations
    Ackermann, Lutz
    Altharnmer, Andreas
    [J]. SYNLETT, 2008, (07) : 995 - 998
  • [2] Catalyst Control of Selectivity in CO2 Reduction Using a Tunable Heterobimetallic Effect
    Bagherzadeh, Sharareh
    Mankad, Neal P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (34) : 10898 - 10901
  • [3] Barton D., 1999, Comprehensive Natural Products Chemistry, V1
  • [4] Asymmetric Hydrogenation of Disubstituted, Trisubstituted, and Tetrasubstituted Minimally Functionalized Olefins and Cyclic β-Enamides with Easily Accessible Ir-P,Oxazoline Catalysts
    Biosca, Maria
    Magre, Marc
    Pamies, Oscar
    Dieguez, Montserrat
    [J]. ACS CATALYSIS, 2018, 8 (11): : 10316 - 10320
  • [5] Borane-Mediated Carbon Dioxide Reduction at Ruthenium: Formation of C1 and C2 Compounds
    Bontemps, Sebastien
    Vendier, Laure
    Sabo-Etienne, Sylviane
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) : 1671 - 1674
  • [6] Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones
    Chen, Qing-An
    Chen, Mu-Wang
    Yu, Chang-Bin
    Shi, Lei
    Wang, Duo-Sheng
    Yang, Yan
    Zhou, Yong-Gui
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16432 - 16435
  • [7] Highly Enantioselective Hydrogenation of Steric Hindrance Enones Catalyzed by Ru Complexes with Chiral Diamine and Achiral Phosphane
    Chen, Xiangning
    Zhou, Han
    Zhang, Kunyu
    Li, Jiawen
    Huang, Hanmin
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 3912 - 3915
  • [8] Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors
    Cinelli, Maris A.
    Li, Huiying
    Chreifi, Georges
    Poulos, Thomas L.
    Silverman, Richard B.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (09) : 3958 - 3978
  • [9] A Modular Furanoside Thioether-Phosphite/Phosphinite/Phosphine Ligand Library for Asymmetric Iridium-Catalyzed Hydrogenation of Minimally Functionalized Olefins: Scope and Limitations
    Coll, Mercedes
    Pamies, Oscar
    Dieguez, Montserrat
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 143 - 160
  • [10] Asymmetric organocatalytic reduction of ketimines with catecholborane employing a N-triflyl phosphoramide Bronsted acid as catalyst
    Enders, Dieter
    Rembiak, Andreas
    Seppelt, Matthias
    [J]. TETRAHEDRON LETTERS, 2013, 54 (06) : 470 - 473
123456