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
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2017年 / 65卷 / 11期
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
  • [31] Elucidating the Mechanism and Chemoselectivity in the PBu3-Catalyzed Rauhut-Currier Reaction of Chalcone with Ethyl Acrylate
    Ye, Juan
    Wang, Yang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (32)
  • [32] The first report of Lewis acid reagents in the intramolecular Rauhut-Currier reaction
    Krasley, Andrew T.
    Malachowski, William P.
    TETRAHEDRON LETTERS, 2015, 56 (44) : 6073 - 6076
  • [33] Asymmetric Intermolecular Rauhut-Currier Reaction for the Construction of 3,3-Disubstituted Oxindoles with Quaternary Stereogenic Centers
    Wang, Hongyu
    Wang, Kaiye
    Man, Yunquan
    Gao, Xiaonan
    Yang, Limin
    Ren, Yanfei
    Li, Na
    Tang, Bo
    Zhao, Gang
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (22) : 3934 - 3939
  • [34] Enantioselective Synthesis of Chromanones via a Peptidic Phosphane Catalyzed Rauhut-Currier Reaction
    Scanes, Robert J. H.
    Grossmann, Oleg
    Grossmann, Andre
    Spring, David R.
    ORGANIC LETTERS, 2015, 17 (10) : 2462 - 2465
  • [35] Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut-Currier Adducts of Nitroalkenes
    Kumar, Tarun
    Mane, Vaijinath
    Namboothiri, Irishi N. N.
    ORGANIC LETTERS, 2017, 19 (16) : 4283 - 4286
  • [36] Facile synthesis of α-methylidene-γ-butyrolactones: intramolecular Rauhut-Currier reaction promoted by chiral acid base organocatalysts
    Takizawa, Shinobu
    Nguyen, Tue Minh-Nhat
    Grossmann, Andre
    Suzuki, Michitaka
    Enders, Dieter
    Sasai, Hiroaki
    TETRAHEDRON, 2013, 69 (03) : 1202 - 1209
  • [37] Acrylamide in Rauhut-Currier reaction; intramolecular isomerization of activated alkenes for quinolone synthesis
    Bharadwaj, Kishor Chandra
    TETRAHEDRON, 2017, 73 (38) : 5690 - 5699
  • [38] Phosphine-Catalyzed Asymmetric Intermolecular Cross Rauhut-Currier Reaction of β-Perfluoroalkyl-Substituted Enones and Vinyl Ketones
    Tao, Mengna
    Zhou, Wei
    Zhang, Junliang
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (19) : 3347 - 3353
  • [39] Evidence for an Enzyme-Catalyzed Rauhut-Currier Reaction during the Biosynthesis of Spinosyn A
    Choi, Sei-Hyun
    Jeon, Byungsun
    Kim, Namho
    Wu, Hsin-Hui
    Ko, Tzu-Ping
    Ruszczycky, Mark W.
    Isiorho, Eta A.
    Liu, Yung-Nan
    Keatinge-Clay, Adrian T.
    Tsai, Ming-Daw
    Liu, Hung-Wen
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (48) : 20291 - 20295
  • [40] Exploration of flow reaction conditions using machine-learning for enantioselective organocatalyzed Rauhut-Currier and [3+2] annulation sequence
    Kondo, Masaru
    Wathsala, H. D. P.
    Sako, Makoto
    Hanatani, Yutaro
    Ishikawa, Kazunori
    Hara, Satoshi
    Takaai, Takayuki
    Washio, Takashi
    Takizawa, Shinobu
    Sasai, Hiroaki
    CHEMICAL COMMUNICATIONS, 2020, 56 (08) : 1259 - 1262
12345