Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation

被引：58
|
作者：
Liu, Chun-Rong [1 ]
Zhu, Ben-Hu [3 ]
Zheng, Jun-Cheng [1 ]
Sun, Xiu-Li [1 ]
Xie, Zuowei [2 ]
Tang, Yong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
[3] Suzhou Univ, Sch Chem & Chem Engn, Suzhou 215123, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 04期
关键词：
ENANTIOSELECTIVE SYNTHESIS; ETHYL DIAZOACETATE; PORPHYRIN COMPLEX; SULFUR YLIDES; ORGANOCATALYTIC CYCLOPROPANATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC EPOXIDATION; SELECTIVE OLEFINATION; ORGANIC-SYNTHESIS; SULFONIUM YLIDES;
D O I：
10.1039/c0cc02347g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, alpha-ylidene-beta-diketones and alpha, beta-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively, in up to 96% yield with high diastereoselectivities.
引用
收藏
页码：1342 / 1344
页数：3
相关论文
共 50 条
  • [31] Modular Domino Process toward Highly Functionalized Pyrroles via Pd-Catalyzed [4+1] Annulation under Mild Conditions
    Zuo, Linhong
    Yang, Yulian
    Guo, Wusheng
    ORGANIC LETTERS, 2021, 23 (06) : 2013 - 2018
  • [32] Iridium-Catalyzed Formal [4+1] Annulation of Benzamides and Cyclopropanols to Afford Isoindolin-1-one Derivatives via C-H Activation
    Xu, Shuran
    Luo, Cankun
    Yan, Kaichuan
    Li, Jianglian
    Lai, Ruizhi
    Hai, Li
    Guan, Mei
    Wu, Yong
    SYNTHESIS-STUTTGART, 2022, 54 (13): : 3015 - 3024
  • [33] Co(III)-Catalyzed [4+1] Annulation of Amides with Allenes via C-H Activation
    Boobalan, Ramadoss
    Santhoshkumar, Rajagopal
    Cheng, Chien-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) : 1140 - 1145
  • [34] Rhodium-Catalyzed Reaction of Sulfoxonium Ylides and Anthranils toward Indoloindolones via a (4+1) Annulation
    Wu, Xiaopeng
    Xiao, Yan
    Sun, Song
    Yu, Jin-Tao
    Cheng, Jiang
    ORGANIC LETTERS, 2019, 21 (17) : 6653 - 6657
  • [35] Palladium-Catalyzed Formal [4+1] Annulation via Metal Carbene Migratory Insertion and C(sp2) -H Bond Functionalization
    Xu, Shuai
    Chen, Ri
    Fu, Zihao
    Zhou, Qj
    Zhang, Yan
    Wang, Jianbo
    ACS CATALYSIS, 2017, 7 (03): : 1993 - 1997
  • [36] Stereocontrolled [4+1] Annulation of -Hydroxycyclobutenones: Synthesis of Polysubstituted Cyclopentenones
    Mao, Xu
    Song, Peidong
    Hao, Yu
    Sun, Zezhong
    Hu, Xiangdong
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3719 - 3723
  • [37] Pd(II)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans
    Shi, Taoda
    Guo, Xin
    Teng, Shenghan
    Hu, Wenhao
    CHEMICAL COMMUNICATIONS, 2015, 51 (82) : 15204 - 15207
  • [38] Synthesis of 2-indanones via [4+1] annulation reactions of (trialkylsilyl)arylketenes.
    Davie, CP
    Zhang, YJ
    Dalton, AM
    Danheiser, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U112 - U113
  • [39] Formal [4+1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles
    Zhang, Qian
    Yu, Mangfei
    Yuan, Jingwen
    Zhang, Rui
    Liang, Yongjiu
    Tian, Jiamei
    Dong, Dewen
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14): : 6036 - 6041
  • [40] Synthesis of substituted dihydro-1H-pyrazoles and 1H-pyrazoles via formal [4+1] annulation of α-arylhydrazonoketones and dimethyl sulfonium methylides
    Deng, Bicheng
    Li, Chaoran
    Yuan, Jingwen
    Rao, Chitturi Bhujanga
    Zhao, Yanning
    Zhang, Rui
    Dong, Dewen
    TETRAHEDRON, 2019, 75 (15) : 2273 - 2279
12345