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
  • [21] Phosphine-Catalyzed Chemoselective [4+3] Cycloaddition of Alminine Esters and β′-acetoxy Allenoates for Divergent Synthesis of Azepines
    Dai, Zonghao
    Zhu, Jin
    Wang, Jiahua
    Su, Wenbo
    Yang, Fulai
    Zhou, Qingfa
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 545 - 551
  • [22] Phosphine-Catalyzed Dearomative [3+2] Cycloaddition of Benzoxazoles with a Cyclopropenone
    Wang, Xingben
    Yu, Congjun
    Atodiresei, Iuliana L.
    Patureau, Frederic W.
    ORGANIC LETTERS, 2022, 24 (05) : 1127 - 1131
  • [23] Phosphine-Catalyzed Annulation Reactions of 2-Butynoate and α-Keto Esters: Synthesis of Cyclopentene Derivatives
    Mbofana, Curren T.
    Miller, Scott J.
    ACS CATALYSIS, 2014, 4 (10): : 3671 - 3674
  • [24] Phosphine-catalyzed [4+2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives
    Ma, Shanshan
    Yu, Aimin
    Meng, Xiangtai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (16) : 2885 - 2892
  • [25] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
    Du, YS
    Lu, XY
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16): : 6463 - 6465
  • [26] An unexpected phosphine-catalyzed [3+2] annulation. Synthesis of highly functionalized cyclopentenes
    Lu, Zheng
    Zheng, Suqing
    Zhang, Xumu
    Lu, Xiyan
    ORGANIC LETTERS, 2008, 10 (15) : 3267 - 3270
  • [27] Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation
    Andrews, Ian P.
    Kwon, Ohyun
    CHEMICAL SCIENCE, 2012, 3 (08) : 2510 - 2514
  • [28] Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines
    Zhang, Fuhao
    Dai, Xuan
    Dai, Lei
    Zheng, Wenrui
    Chan, Wai-Lun
    Tang, Xiaodong
    Zhang, Xumu
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (24)
  • [29] Phosphine-catalyzed (3+2)/(2+3) sequential annulation involving a triple nucleophilic addition reaction of γ-vinyl allenoates
    Feng, Jiaxu
    Huang, You
    CHEMICAL COMMUNICATIONS, 2019, 55 (93) : 14011 - 14014
  • [30] Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates
    Cerveri, Alessandro
    Nieto Faza, Olalla
    Silva Lopez, Carlos
    Grilli, Stefano
    Monari, Magda
    Bandini, Marco
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6347 - 6355
12345