Enantioselective construction of substituted hydantoins via chiral phosphoric acid catalyzed annulation/Heyns rearrangement of aryl-substituted ureas with glyoxals

被引：4
|
作者：
Wang, Yong [1 ,2 ]
Li, Jingyuan [3 ]
Li, Yanyan [1 ,2 ]
Pi, Chao [1 ,2 ]
Wu, Yangjie [1 ,2 ]
Cui, Xiuling [1 ,2 ]
机构：
[1] Zhengzhou Univ, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Green Catalysis Ctr, 75 Daxue Rd North, Zhengzhou 450052, Peoples R China
[2] Zhengzhou Univ, Coll Chem, 75 Daxue Rd North, Zhengzhou 450052, Peoples R China
[3] Shanghai Jiao Tong Univ, Schl Chem & Chem Engn, Shanghai 200240, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 22期
关键词：
DERIVATIVES;
D O I：
10.1039/d3qo01194a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, the de novo organocatalyzed enantioselective construction of hydantoins from simple urea and glyoxal is reported. A chiral phosphoric acid (CPA) catalyzed [3 + 2] heteroannulation/enantioselective Heyns rearrangement is proposed to be involved in this transformation. The Heyns rearrangement smoothly proceeded via a proton-transfer process involving an enol intermediate. The CPA served as a chiral proton-transfer shuttle to control the enantioselectivity.
引用
收藏
页码：5631 / 5636
页数：6
相关论文
共 50 条
  • [21] Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs
    Chiminazzo, Andrea
    Sperni, Laura
    Scarso, Alessandro
    Strukul, Giorgio
    CATALYSTS, 2017, 7 (03)
  • [22] An effective approach to aryl-substituted propanoic acids via the Pd-catalyzed hydrocarboxylation of stilbenes
    Dai, Jie
    Ren, Wenlong
    Li, Jingfu
    Shi, Yian
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 561 - 565
  • [23] Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition
    Varlet, Thomas
    Matisic, Mateja
    Van Elslande, Elsa
    Neuville, Luc
    Gandon, Vincent
    Masson, Geraldine
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (30) : 11611 - 11619
  • [24] Kinetic Resolution in Chiral Phosphoric Acid Catalyzed Aldol Reactions: Enantioselective Robinson-Type Annulation Reactions
    Yamanaka, Masahiro
    Hoshino, Masaya
    Katoh, Takuya
    Mori, Keiji
    Akiyama, Takahiko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) : 4508 - 4514
  • [25] Phosphoric Acid Catalyzed Diastereo- and Enantioselective Synthesis of Substituted 1,3-Diaminotetralins
    Dagousset, Guillaume
    Erb, William
    Zhu, Jieping
    Masson, Geraldine
    ORGANIC LETTERS, 2014, 16 (09) : 2554 - 2557
  • [26] Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines
    Ma, Wei-Yang
    Gelis, Coralie
    Bouchet, Damien
    Retailleau, Pascal
    Moreau, Xavier
    Neuville, Luc
    Masson, Geraldine
    ORGANIC LETTERS, 2021, 23 (02) : 442 - 448
  • [27] SYNTHESIS OF ARYL-SUBSTITUTED ALLYLIC AMINES VIA PALLADIUM-CATALYZED COUPLING OF ARYL IODIDES, NONCONJUGATED DIENES, AND AMINES
    LAROCK, RC
    WANG, Y
    LU, YD
    RUSSELL, CE
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26): : 8107 - 8114
  • [28] Chiral Bronsted acid catalyzed enantioselective intermolecular desymmetrizations of 3-substituted azetidines
    Wang, Zhaobin
    Sun, Jianwei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [29] Enantioselective Synthesis of Cyclohexenol Derivatives from γ-Aryl-Substituted Enals via an Organocatalyzed Three-Component Reaction
    Majee, Debashis
    Jakkampudi, Satish
    Arman, Hadi D.
    Zhao, John C. -G.
    ORGANIC LETTERS, 2019, 21 (22) : 9166 - 9170
  • [30] Copper-Catalyzed Asymmetric Conjugate Addition of Aryl Aluminum Reagents to Trisubstituted Enones: Construction of Aryl-Substituted Quaternary Centers
    Hawner, Christine
    Li, Kangying
    Cirriez, Virginie
    Alexakis, Alexandre
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) : 8211 - 8214
12345