Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium

被引：43
作者：
Gillard, Rachel M. [1 ]
Fernando, Jared E. M. [1 ]
Lupton, David W. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 17期
基金：
澳大利亚研究理事会;
关键词：
1,6-addition; dienyl acyl azolium; enantioselective catalysis; N-heterocyclic carbene; beta-lactonization; INTRAMOLECULAR STETTER REACTION; SUBSTITUTED BETA-LACTONES; CARBON 4+2 ANNULATION; ASYMMETRIC-SYNTHESIS; LEWIS-ACID; CYCLOADDITION REACTION; DISUBSTITUTED KETENES; DOMINO REACTIONS; DELTA-LACTONES; NHC CATALYSIS;
D O I：
10.1002/anie.201712604
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein we report the enantioselective N-heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio- and diastereo-enriched cyclohexenes (most > 97:3 er and > 20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6-addition/beta-lactonization.
引用
收藏
页码：4712 / 4716
页数：5
相关论文
共 85 条
  • [21] NHC-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Activation
    De Sarkar, Suman
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9266 - 9269
  • [22] Beyond Classical Reactivity Patterns: Shifting from 1,4-to 1,6-Additions in Regio- and Enantioselective Organocatalyzed Vinylogous Reactions of Olefinic Lactones with Enals and 2,4-Dienals
    Dell'Amico, Luca
    Albrecht, Lukasz
    Naicker, Tricia
    Poulsen, Pernille H.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) : 8063 - 8070
  • [23] Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
  • [24] Organocatalysis by N-heterocyclic, carbenes
    Enders, Dieter
    Niemeier, Oliver
    Henseler, Alexander
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5606 - 5655
  • [25] Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
    Flanigan, Darrin M.
    Romanov-Michailidis, Fedor
    White, Nicholas A.
    Rovis, Tomislav
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9307 - 9387
  • [26] Grossmann A., 2012, Angew. Chem, V124, P320, DOI DOI 10.1002/ANIE.201105415
  • [27] N-Heterocyclic Carbene Catalyzed Domino Reactions
    Grossmann, Andre
    Enders, Dieter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) : 314 - 325
  • [28] Asymmetric organocatalysis of 4+3 cycloaddition reactions
    Harmata, M
    Ghosh, SK
    Hong, XC
    Wacharasindhu, S
    Kirchhoefer, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) : 2058 - 2059
  • [29] Formal cycloaddition of disubstituted ketenes with 2-oxoaldehydes catalyzed by chiral N-heterocyclic carbenes
    He, Lin
    Lv, Hui
    Zhang, Yan-Rong
    Ye, Song
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) : 8101 - 8103
  • [30] An overview of N-heterocyclic carbenes
    Hopkinson, Matthew N.
    Richter, Christian
    Schedler, Michael
    Glorius, Frank
    [J]. NATURE, 2014, 510 (7506) : 485 - 496
123456789