Gold(I) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines

被引：19
|
作者：
Sun, Yuan-Ming [1 ,2 ,3 ]
Gu, Peng [1 ,2 ,3 ]
Gao, Yu-Ning [1 ,2 ,3 ]
Xu, Qin [1 ,2 ,3 ]
Shi, Min [1 ,2 ,3 ,4 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] 130 MeiLong Rd, Shanghai 200237, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 42期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTION; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; 1,6-DIYNE ESTERS; CYCLOISOMERIZATION; CYCLOADDITION; 1,2-ACYLOXY; REARRANGEMENT; MIGRATION; 3-ACYLOXY-1,4-ENYNES;
D O I：
10.1039/c6cc03132c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An effective synthetic protocol for structurally diverse 4-acyloxy-1,2-dihydroquinoline compounds has been accomplished by a gold(I)-catalyzed tandem [3,3]-rearrangement and intramolecular hydroamination of propargylic esters, affording the desired products in good yields. Moreover, the asymmetric variant of this cyclization has also been achieved using a chiral nitrogen acyclic carbene (NAC) gold(I) complex. These products have application in the enantioselective synthesis of an aromatase inhibitor within three simple steps.
引用
收藏
页码：6942 / 6945
页数：4
相关论文
共 50 条
  • [1] Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-Catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions
    Liu, Xin-Yuan
    Ding, Pan
    Huang, Jie-Sheng
    Che, Chi-Ming
    [J]. ORGANIC LETTERS, 2007, 9 (14) : 2645 - 2648
  • [2] Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush"
    Shu, Xing-Zhong
    Shu, Dongxu
    Schienebeck, Casi M.
    Tang, Weiping
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (23) : 7698 - 7711
  • [3] Enantioselective Synthesis of 4-Allyl Tetrahydroquinolines via Copper(I) Hydride-Catalyzed Hydroallylation of 1,2-Dihydroquinolines
    Xu-Xu, Qing-Feng
    Zhang, Xiao
    You, Shu-Li
    [J]. ORGANIC LETTERS, 2020, 22 (04) : 1530 - 1534
  • [4] Gold(I)-Catalyzed Intramolecular Cycloisomerization of Propargylic Esters with Furan Rings
    Yang, Jin-Ming
    Tang, Xiang-Ying
    Shi, Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (12) : 4534 - 4540
  • [5] Highly Efficient Synthesis of Polysubstituted 1,2-Dihydroquinolines via Tandem Reaction of α-Ketoesters and Arylamines Catalyzed by Indium Triflate
    Zhang, Ji-Chen
    Ji, Jian-Xin
    [J]. ACS CATALYSIS, 2011, 1 (10): : 1360 - 1363
  • [6] Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines
    Jiao, Mingdong
    Gao, Jihui
    Fang, Xianjie
    [J]. ORGANIC LETTERS, 2020, 22 (21) : 8566 - 8571
  • [7] Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines
    Chandrasekhar, B.
    Ahn, Sewon
    Ryu, Jae-Sang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6740 - 6749
  • [8] Gold(I)-Catalyzed Tandem Cyclization Approach to Tetracyclic Indolines
    Liu, Yongxiang
    Xu, Wenqing
    Wang, Xiang
    [J]. ORGANIC LETTERS, 2010, 12 (07) : 1448 - 1451
  • [9] Gold catalyzed cyclization of propargylic esters with enones to give Rauhut-Currier type products
    Cran, John W.
    Krafft, Marie E.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [10] Gold(I)-Catalyzed Tandem Reaction of γ-Amino-Substituted Propargylic Esters to Pyrrolines and its Application in the Formal Synthesis of (±)-Aphanorphine
    Wang, Zhengshen
    Zheng, Huaiji
    Yang, Juan
    Xie, Xingang
    She, Xuegong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2082 - 2088
12345