Merging Chiral Bronsted Acid/Base Catalysis: An Enantioselective [4+2] Cycloaddition of o-Hydroxystyrenes with Azlactones

被引：101
|
作者：
Zhang, Yu-Chen
Zhu, Qu-Ning
Yang, Xue
Zhou, Lu-Jia
Shi, Feng [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 04期
关键词：
ORTHO-QUINONE METHIDES; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; BICYCLIC GUANIDINE; POVAROV REACTION; ACID; METAL; CONSTRUCTION; ACTIVATION; ANNULATION;
D O I：
10.1021/acs.joc.6b00078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective [4 + 2] cycloaddition of o-hydroxylstyrenes with azlactones has been established by merging chiral Bronsted acid (chiral phosphoric acid) and base (chiral guanidine) catalysis, which constructed a biologically important dihydrocoumarin scaffold in an efficient and enantioselective style (up to 99% yield, 96:4 er). This approach has not only realized the successful application of o-hydroxylstyrenes as oxa-diene precursors in catalytic asymmetric cycloadditions but also established a new cooperative catalytic system of chiral phosphoric acid and chiral guanidine.
引用
收藏
页码：1681 / 1688
页数：8
相关论文
共 50 条
  • [1] Catalytic Asymmetric [4+2] Cycloaddition of in Situ Generated o-Quinone Methide (mines with o-Hydroxystyrenes: Diastereo- and Enantioselective Construction of Tetrahydroquinoline Frameworks
    Li, Lin-Zhi
    Wang, Cong-Shuai
    Guo, Wei-Feng
    Mei, Guang-Jian
    Shi, Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 614 - 623
  • [2] N-Heterocyclic Carbene and Chiral Bronsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation
    Chen, Dian-Feng
    Rovis, Tomislav
    SYNTHESIS-STUTTGART, 2017, 49 (02): : 293 - 298
  • [3] Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis
    Denmark, Scott E.
    Burk, Matthew T.
    ORGANIC LETTERS, 2012, 14 (01) : 256 - 259
  • [4] Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base
    Terada, Masahiro
    Nii, Hiroyuki
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) : 1760 - 1763
  • [5] Oxathiaborolium-Catalyzed Enantioselective [4+2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4+2] Cycloaddition
    Boobalan, Ramalingam
    Chein, Rong-Jie
    ORGANIC LETTERS, 2021, 23 (17) : 6760 - 6764
  • [6] Chiral Phosphoric Acid Catalyzed Enantioselective [4+2] Cycloaddition Reaction of α-Fluorostyrenes with Imines
    Kikuchi, Jun
    Ye, Haiting
    Terada, Masahiro
    ORGANIC LETTERS, 2020, 22 (22) : 8957 - 8961
  • [7] Enantioselective Bronsted base catalyzed [4+2] cycloaddition using novel amino-substituted tetraphenylene derivatives
    Hau, Chun-Kit
    He, Hao
    Lee, Albert W. M.
    Chik, David T. W.
    Cai, Zongwei
    Wong, Henry N. C.
    TETRAHEDRON, 2010, 66 (52) : 9860 - 9874
  • [8] Enantioselective Cross-[4+2]-Cycloaddition/Decarboxylation of 2-Pyrones by Cooperative Catalysis of the Pd(0)/NHC Complex and Chiral Phosphoric Acid
    Xu, Meng-Meng
    Xie, Pei-Pei
    He, Jun-Xiong
    Zhang, Yu-Zhen
    Zheng, Chao
    Cai, Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (10) : 6936 - 6946
  • [9] Bronsted acid mediated intramolecular cyclopropane ring expansion/[4+2]-cycloaddition
    Li, Jian
    Zhu, Shangrong
    Xu, Qiuneng
    Liu, Li
    Yan, Shenghu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (47) : 10004 - 10008
  • [10] Application of Chiral Lewis Base/Bronsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides
    Zhu Deng
    Chen Zhi-Min
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3015 - 3032
12345