Phosphine-Catalyzed [3+2] Annulations with γ-Methyl Allenoates

被引：9
|
作者：
Ma, Rong [1 ]
Song, Gege [1 ]
Xi, Qiuzhen [1 ]
Yang, Liu [1 ]
Li, Er-Qing [1 ]
Duan, Zheng [1 ]
机构：
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 39卷 / 08期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
phosphine-catalyzed; gamma-methyl allenoates; 3+2] annulation; ALLYLIC PHOSPHORUS YLIDES; SUBSTITUTED ALLENOATES; DOMINO REACTION; CYCLOADDITION; CONSTRUCTION; ALLENES; IMINES; DERIVATIVES; REACTIVITY; PROGRESS;
D O I：
10.6023/cjoc201901040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The phosphine-catalyzed [3+2] annulation of gamma-methyl allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is reported. In the reaction, a series of highly functionalized spiro[4.4] dec-6-ene skeletons were obtained in moderate to good yields and high diastereoselectivities. It should be noted that the perfect alpha-regioselective annulation adducts were obtained with simple PPh3 catalyst.
引用
收藏
页码：2196 / 2202
页数：7
相关论文
共 41 条
  • [1] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters
    Bencivenni, Giorgio
    Wu, Li-Yuan
    Mazzanti, Andrea
    Giannichi, Berardino
    Pesciaioli, Fabio
    Song, Mao-Ping
    Bartoli, Giuseppe
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) : 7200 - 7203
  • [2] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters
    Cao, Yiming
    Jiang, Xianxing
    Liu, Luping
    Shen, Fangfang
    Zhang, Futing
    Wang, Rui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9124 - 9127
  • [3] Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of α-Substituted Allenoates
    Chen, Rongshun
    Fan, Xia
    Xu, Zhaozhong
    He, Zhengjie
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) : 1469 - 1473
  • [4] Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes
    Dudding, Travis
    Kwon, Ohyun
    Mercier, Evan
    [J]. ORGANIC LETTERS, 2006, 8 (17) : 3643 - 3646
  • [5] Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications
    Gomez, Catherine
    Gicquel, Maxime
    Carry, Jean-Christophe
    Schio, Laurent
    Retailleau, Pascal
    Voituriez, Arnaud
    Marinetti, Angela
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04): : 1488 - 1496
  • [6] Efficient organocatalyzed solvent-free selective synthesis of conjugated enones
    Goswami, Papori
    Das, Babulal
    [J]. TETRAHEDRON LETTERS, 2009, 50 (08) : 897 - 900
  • [7] Phosphine Organocatalysis
    Guo, Hongchao
    Fan, Yi Chiao
    Sun, Zhanhu
    Wu, Yang
    Kwon, Ohyun
    [J]. CHEMICAL REVIEWS, 2018, 118 (20) : 10049 - 10293
  • [8] Synthesis of Chiral Tetrasubstituted Alkenes by an Asymmetric Cascade Reaction Catalyzed Cooperatively by Cationic Rhodium(I) and Silver(I) Complexes
    Hojo, Daiki
    Noguchi, Keiichi
    Tanaka, Ken
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) : 8129 - 8132
  • [9] Lang R. W., 1990, ORG SYNTH, V62, P202
  • [10] Phosphine-Catalyzed [3+2] Annulation of γ- Substituted Allenoates: Novel Access to Functionalized Cyclopentenes and Bicyclic[3,3,0]octene Derivatives
    Li, Erqing
    Jin, Hongxing
    Huang, You
    [J]. CHEMISTRYSELECT, 2018, 3 (42): : 12007 - 12010
12345