Iridium-Catalyzed Enantioselective Allylic Alkynylation

被引：135
|
作者：
Hamilton, James Y. [1 ]
Sarlah, David [1 ]
Carreira, Erick M. [1 ]
机构：
[1] ETH, CH-8093 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 29期
基金：
瑞士国家科学基金会;
关键词：
alkynes; alkynyltrifluoroborates; allylic substitution; enantioselectivity; iridium; ASYMMETRIC ADDITION; CONJUGATE ADDITION; ALKYLATIONS; TRIFLUOROBORATE; SUBSTITUTION; ALLYLATION; AMINATION; ALDEHYDES; ESTERS; ACID;
D O I：
10.1002/anie.201302731
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod=1,5-cyclooctadiene. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7532 / 7535
页数：4
相关论文
共 50 条
  • [1] Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols
    Lafrance, Marc
    Roggen, Markus
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3470 - 3473
  • [2] Enantioselective Iridium-Catalyzed Allylic Arylation
    Polet, Damien
    Rathgeb, Xavier
    Falciola, Caroline A.
    Langlois, Jean-Baptiste
    El Hajjaji, Samir
    Alexakis, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) : 1205 - 1216
  • [3] Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols
    Guo, Jia
    Ma, Hao-Ran
    Xiong, Wen-Bin
    Fan, Luoyi
    Zhou, You-Yun
    Wong, Henry N. C.
    Cui, Jian-Fang
    CHEMICAL SCIENCE, 2022, 13 (46) : 13914 - 13921
  • [4] Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7644 - 7647
  • [5] Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation
    Butcher, Trevor W.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13125 - 13129
  • [6] Enantioselective Iridium-Catalyzed Allylic Cyclizations
    Schafroth, Michael A.
    Rummelt, Stephan M.
    Sarlah, David
    Carreira, Erick M.
    ORGANIC LETTERS, 2017, 19 (12) : 3235 - 3238
  • [7] Iridium-Catalyzed Enantioselective Allylic Substitution
    Takeuchi, Ryo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (09) : 885 - 902
  • [8] Iridium-Catalyzed Asymmetric Allylic Aromatization Reaction
    Liu, Xi-Jia
    Zheng, Chao
    Yang, Yi-Han
    Jin, Shicheng
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (31) : 10493 - 10499
  • [9] Iridium-Catalyzed Allylic Substitution
    Hartwig, John F.
    Pouy, Mark J.
    IRIDIUM CATALYSIS, 2011, 34 : 169 - 208
  • [10] Enantioselective Iridium-Catalyzed Allylic Substitution with 2-Methylpyridines
    Liu, Xi-Jia
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 4002 - 4005
12345