Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

被引：26
|
作者：
Andrews, Ian P.
Blank, Brian R.
Kwon, Ohyun
机构：
来源：
CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 43期
关键词：
HIGHLY DIASTEREOSELECTIVE SYNTHESIS; DOUBLE-MICHAEL REACTIONS; 3+2 CYCLOADDITION; 4+2 ANNULATION; ALLENOATE ADDITIONS; IMINES; ALLENES; 2,3-BUTADIENOATES; DIHYDROPYRONES; HETEROCYCLES;
D O I：
10.1039/c2cc31347b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An array of N-tosylated alpha-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The alpha-aminoalkylallenic esters were prepared through aza-Baylis-Hillman reactions or novel DABCO-mediated decarboxylative rearrangements of allenylic carbamates. Conversion of these substrates to 3-carbethoxy-2-alkyl-3-pyrrolines was facilitated through Ph3P-catalyzed intramolecular gamma-umpolung addition.
引用
收藏
页码：5373 / 5375
页数：3
相关论文
共 50 条
  • [41] Dearomatization of 3-Nitroindoles by a Phosphine-Catalyzed Enantioselective [3+2] Annulation Reaction
    Li, Kaizhi
    Goncalves, Theo P.
    Huang, Kuo-Wei
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) : 5427 - 5431
  • [42] Phosphine-catalyzed [3+2] and [3+3] Annulations of Azomethine Imines with Ethyl 2-Butynoate
    Liu, Jun
    Liu, Honglei
    Na, Risong
    Wang, Guiyong
    Li, Zhen
    Yu, Hao
    Wang, Min
    Zhong, Jiangchun
    Guo, Hongchao
    CHEMISTRY LETTERS, 2012, 41 (03) : 218 - 220
  • [43] Phosphine-Catalyzed Annulations Based on [3+3] and [3+2] Trapping of Ketene Intermediates with Thioamides
    Wang, Yu-Hao
    Zhao, Zhen-Ni
    Kalita, Subarna Jyoti
    Huang, Yi-Yong
    ORGANIC LETTERS, 2021, 23 (21) : 8147 - 8152
  • [44] Phosphine-catalyzed highly diastereoselective [3+2] cyclization of isatin derived electron-deficient alkenes with α-allenic esters
    Zhang, Xiu-Chun
    Cao, Shu-Hua
    Wei, Yin
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2011, 47 (05) : 1548 - 1550
  • [45] Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans
    Wang, Huamin
    Zhang, Junyou
    Tu, Youshao
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) : 5422 - 5426
  • [46] Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of α-Substituted Allenoates
    Chen, Rongshun
    Fan, Xia
    Xu, Zhaozhong
    He, Zhengjie
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) : 1469 - 1473
  • [47] Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones
    Neel, Mathilde
    Gouin, Jerome
    Voituriez, Arnaud
    Marinetti, Angela
    SYNTHESIS-STUTTGART, 2011, (12): : 2003 - 2009
  • [48] Phosphine-Catalyzed [3+2] Cycloaddition of Aza-Aurones and Allenoates: Enantioselective Synthesis of 2-Spirocyclopentyl-Indolin-3-Ones
    Brambilla, Elisa
    Pozza, Camilla
    Rizzato, Silvia
    Abbiati, Giorgio
    Pirovano, Valentina
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (03)
  • [49] Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2]?Annulations
    Duvvuru, Deepti
    Pinto, Nathalie
    Gomez, Catherine
    Betzer, Jean-Francois
    Retailleau, Pascal
    Voituriez, Arnaud
    Marinetti, Angela
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) : 408 - 414
  • [50] Hydroxy-assisted regio- and stereoselective synthesis of functionalized alkenes via phosphine-catalyzed β′-umpolung addition of o-hydroxy aromatic aldimines to allenoates
    Cheng, Kunpeng
    Bao, Yishu
    Wang, Jiahua
    Dai, Zonghao
    Lu, Jinrong
    Zhou, Qingfa
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (15): : 2375 - 2378
12345