Chiral Organocatalyzed Intermolecular Rauhut-Currier Reaction of Nitroalkenes with Ethyl Allenoate

被引:6
|
作者
Takizawa, Shinobu [1 ]
Sako, Makoto [1 ]
Kishi, Kenta [1 ]
Shigenobu, Masashi [1 ]
Vo-Thanh, Giang [2 ]
Sasai, Hiroaki [1 ]
机构
[1] Osaka Univ, ISIR, Ibaraki, Osaka 5670047, Japan
[2] Univ Paris Saclay, Univ Paris Sud, Lab Catalyse Mol, ICMMO,UMR8182, F-91405 Orsay, France
关键词
Rauhut-Currier reaction; chiral organocatalysis; nitroalkene; alpha-functionalized allenoate; MORITA-BAYLIS-HILLMAN; ROUTE;
D O I
10.1248/cpb.c17-00554
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An enantioselective intermolecular Rauhut-Currier (RC) reaction of nitroalkenes with ethyl allenoate has been established with quinidine-derived beta-isocupreidine. The present RC reaction afforded alpha-functionalized allenoates 3 in up to 94% yield with 59% enantiomeric excess (ee).
引用
收藏
页码:997 / 999
页数:3
相关论文
共 50 条
  • [41] Optically active helical polyisocyanides bearing chiral phosphine pendants: Facile synthesis and application in enantioselective Rauhut-Currier reaction
    Li Zhou
    Ling Shen
    Jian Huang
    Na Liu
    Yuan-Yuan Zhu
    Zong-Quan Wu
    Chinese Journal of Polymer Science, 2018, 36 : 163 - 170
  • [42] Optically active helical polyisocyanides bearing chiral phosphine pendants: Facile synthesis and application in enantioselective Rauhut-Currier reaction
    Zhou, Li
    Shen, Ling
    Huang, Jian
    Liu, Na
    Zhu, Yuan-Yuan
    Wu, Zong-Quan
    CHINESE JOURNAL OF POLYMER SCIENCE, 2018, 36 (02) : 163 - 170
  • [43] Optically Active Helical Polyisocyanides Bearing Chiral Phosphine Pendants: Facile Synthesis and Application in Enantioselective Rauhut-Currier Reaction
    Li Zhou
    Ling Shen
    Jian Huang
    Na Liu
    Yuan-Yuan Zhu
    Zong-Quan Wu
    Chinese Journal of Polymer Science, 2018, 36 (02) : 163 - 201
  • [44] Enantioselective Rauhut-Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
    Pitchumani, Venkatachalam
    Breugst, Martin
    Lupton, David W.
    ORGANIC LETTERS, 2021, 23 (24) : 9413 - 9418
  • [45] Organocatalytic Enantioselective Cross-Vinylogous Rauhut-Currier Reaction of Methyl Coumalate with Enals
    Liu, Qiwen
    Zu, Liansuo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (30) : 9505 - 9509
  • [46] Ferrocene-based bifunctional organocatalyst for highly enantioselective intramolecular Rauhut-Currier reaction
    Zhou, Xiaowei
    Nie, Huifang
    Liu, Xian
    Long, Xiaomei
    Jiang, Ru
    Chen, Weiping
    CATALYSIS COMMUNICATIONS, 2019, 121 : 78 - 83
  • [47] Enantioselective N-Heterocyclic Carbene Catalyzed Bis(enoate) Rauhut-Currier Reaction
    Bae, Song
    Zhang, Changhe
    Gillard, Rachel M.
    Lupton, David W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (38) : 13370 - 13374
  • [48] Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction
    Stevanovic, Dragana
    Bugarinovic, Jovana
    Pesic, Marko
    Todosijevic, Anka
    Bogdanovic, Goran A.
    Damljanovic, Ivan
    RSC ADVANCES, 2021, 11 (57) : 36208 - 36214
  • [49] Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem
    Reynolds, Troy E.
    Binkley, Michael S.
    Scheidt, Karl A.
    ORGANIC LETTERS, 2008, 10 (12) : 2449 - 2452
  • [50] DMAP catalysed vinylogous Rauhut-Currier reaction of allenoates with para-quinone methides
    Reddy, Venkatram R.
    Maripally, Narsimulu
    Mutyala, Raghupathi
    Nanubolu, Jagadeesh Babu
    Chandra, Rajesh
    TETRAHEDRON LETTERS, 2018, 59 (27) : 2631 - 2635