Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles

被引:9
|
作者
Sripada, Archita [1 ]
Wolf, Christian [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 17期
基金
美国国家卫生研究院;
关键词
QUATERNARY STEREOGENIC CENTERS; STEREOSELECTIVE-SYNTHESIS; MANNICH REACTIONS; EFFICIENT ACCESS; CONSTRUCTION;
D O I
10.1021/acs.joc.2c01414
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium(phosphinoxazoline) catalyzed method for asymmetric allylic alkylation of alpha-aryl-alpha-fluoroacetonitriles is introduced. This reaction achieves C-C bond formation and incorporation of two adjacent chirality centers with moderate to good yields, high enantioselectivities, and up to 15:1 dr.
引用
收藏
页码:11880 / 11887
页数:8
相关论文
共 50 条
  • [21] Organocatalytic peroxy-asymmetric allylic alkylation
    Feng, Xin
    Yuan, Yu-Qing
    Cui, Hai-Lei
    Jiang, Kun
    Chen, Ying-Chun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (18) : 3660 - 3662
  • [22] ASYMMETRIC ALKYLATION OF ALLYLIC GEM-DICARBOXYLATES
    TROST, BM
    LEE, CB
    WEISS, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) : 7247 - 7248
  • [23] Asymmetric alkylation of allylic gem-dicarboxylates.
    Trost, BM
    Lee, CB
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 416 - ORGN
  • [24] Asymmetric allylic alkylation by palladium-bisphosphinites
    Sharma, Rakesh K.
    Nethaji, Munirathnam
    Samuelson, Ashoka G.
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (06) : 655 - 663
  • [25] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate
    Burger, EC
    Tunge, JA
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 4113 - 4115
  • [26] Copper-catalyzed asymmetric allylic alkylation
    Falciola, Caroline A.
    Alexakis, Alexandre
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (22) : 3765 - 3780
  • [27] Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling
    Hornillos, Valentin
    van Zijl, Anthoni W.
    Feringa, Ben L.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (31) : 3712 - 3714
  • [28] Planar chiral alkenylferrocene phosphanes:: Preparation, structural characterisation and catalytic use in asymmetric allylic alkylation
    Stepnicka, Petr
    Lamac, Martin
    Cisarova, Ivana
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (03) : 446 - 456
  • [29] Asymmetric Allylic Alkylation of -Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst
    Kita, Yusuke
    Kavthe, Rahul D.
    Oda, Hiroaki
    Mashima, Kazushi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (03) : 1098 - 1101
  • [30] Cooperative Catalytic Asymmetric Three-Component Allylic Alkylation Enabled by Ternary Catalyst System
    Gong Liu-Zhu
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (02) : 652 - 653