Phosphine-Catalyzed (4+2) Annulation of Allenoates Bearing Acidic Hydrogen with 1,1-Dicyanoalkenes

被引：4
|
作者：
Gao, Zhenzhen [1 ]
Zhou, Xiaoming [1 ]
Xie, Lei [1 ]
Wang, Xuekun [1 ]
Wang, Shiben [1 ]
Liu, Honglei [2 ]
Guo, Hongchao [3 ]
机构：
[1] Liaocheng Univ, Sch Pharmaceut Sci, Liaocheng 252059, Shandong, Peoples R China
[2] Qingdao Univ, Coll Mat Sci & Engn, Qingdao 266071, Shandong, Peoples R China
[3] China Agr Univ, Innovat Ctr Pesticide Res, Dept Chem, Beijing 100193, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 10期
关键词：
ELECTRON-DEFICIENT OLEFINS; BAYLIS-HILLMAN CARBONATES; ASYMMETRIC-SYNTHESIS; SEQUENTIAL ANNULATION; 3+2 CYCLOADDITIONS; CHIRAL PHOSPHINES; FACILE SYNTHESIS; ALLENES; DERIVATIVES; 2,3-BUTADIENOATES;
D O I：
10.1021/acs.joc.4c00564
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha-succinimide-substituted allenoates were employed as phosphine acceptors in phosphine-catalyzed (4 + 2) annulation with 1,1-dicyanoalkenes. They served as C4 synthons in the annulation reaction under mild reaction conditions and produced hexahydroisoindole derivatives in moderate to high yields with good to excellent diastereoselectivities.
引用
收藏
页码：7169 / 7174
页数：6
相关论文
共 50 条
  • [41] Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates
    Jing, Chengfeng
    Na, Risong
    Wang, Bo
    Liu, Hongle
    Zhang, Lei
    Liu, Jun
    Wang, Min
    Zhong, Jiangchun
    Kwon, Ohyun
    Guo, Hongchao
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1023 - 1034
  • [42] Highly Substituted Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of Electron-deficient Dienes and Vinyl Ketones
    Chen, Peng
    Zhang, Junyou
    Zhang, Junliang
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 682 - 685
  • [43] Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation
    Han, Xiaoyu
    Yao, Weijun
    Wang, Tianli
    Tan, Yong Ren
    Yan, Ziyu
    Kwiatkowski, Jacek
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5643 - 5647
  • [44] Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: access to the synthesis of chromeno[4,3-b]pyrroles
    Li, Xiaohu
    Huang, You
    CHEMICAL COMMUNICATIONS, 2021, 57 (77) : 9934 - 9937
  • [45] Mechanisms of phosphine-catalyzed [4+3] annulation of allenoates with C, N-cyclic azomethine imines: A DFT investigation
    Xu, Hao
    Zhu, Yanyan
    Guo, Peng
    Liu, Chunmei
    Shan, Jiankai
    Tang, Mingsheng
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2018, 118 (15) : 1
  • [46] PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3- CARBOXYLATE
    Lu, Kui
    Kwon, Ohyun
    ORGANIC SYNTHESES, 2009, 86 : 212 - +
  • [47] Diastereoselective Synthesis of 6-Trifluoromethyl-5,6-dihydropyrans via Phosphine-Catalyzed [4+2] Annulation of α-Benzylallenoates with Ketones
    Wang, Tong
    Ye, Song
    ORGANIC LETTERS, 2010, 12 (18) : 4168 - 4171
  • [48] 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
  • [49] Phosphine-Catalyzed [8+2]-Annulation of Heptafulvenes with Allenoates and Its Asymmetric Variant: Construction of Bicyclo[5.3.0]decane Scaffold
    Gao, Zhenzhen
    Wang, Chang
    Zhou, Leijie
    Yuan, Chunhao
    Xiao, Yumei
    Guo, Hongchao
    ORGANIC LETTERS, 2018, 20 (14) : 4302 - 4305
  • [50] Phosphine-Catalyzed [4+3] Annulation of β′-Acetoxy Allenoates with 1C,3N-Dinucleophiles: Access to Functionalized Azepine Derivatives
    Ni, Chunjie
    Liang, Zhanhang
    Xu, Xiaojuan
    Yu, Fan
    Zhang, Dong
    Chen, Chen
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4784 - 4791
12345