A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center

被引:53
作者
Inokoishi, Yogo [1 ]
Sasakura, Niiha [1 ]
Nakano, Keiji [1 ]
Ichikawa, Yoshiyasu [1 ]
Kotsuki, Hiyoshizo [1 ]
机构
[1] Kochi Univ, Fac Sci, Lab Nat Prod Chem, Akebono, Kochi 7808520, Japan
关键词
ENANTIOSELECTIVE CONJUGATE ADDITION; MICHAEL ADDITION; KETONES; AMINE; ALDEHYDES;
D O I
10.1021/ol100350w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position In high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.
引用
收藏
页码:1616 / 1619
页数:4
相关论文
共 50 条
  • [31] Chiral Iodine-Catalyzed Dearomatizative Spirocyclization for the Enantioselective Construction of an All-Carbon Stereogenic Center
    Zhang, Dong-Yang
    Xu, Lue
    Wu, Hua
    Gong, Liu-Zhu
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (29) : 10314 - 10317
  • [32] Chiral Acid-Catalyzed Asymmetric Nazarov Reaction: Nucleophilic Construction of a Quaternary Asymmetric Center at the α-Position of the Keto Function
    Yaji, Kentaro
    Shindo, Mitsuru
    SYNLETT, 2009, (15) : 2524 - 2528
  • [33] Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters
    Chen, Long
    SYNTHESIS-STUTTGART, 2018, 50 (03): : 440 - 469
  • [34] TiCl4-Promoted Mukaiyama Aldol Reaction of Fluorinated Silyl Enolates for the Construction of a Quaternary Carbon Center
    Wang, Wengui
    Chen, Qing-Yun
    Guo, Yong
    SYNLETT, 2011, (18) : 2705 - 2708
  • [35] Organocatalytic Asymmetric Michael Addition of Pyrazolin-5-ones to Nitroolefins with Bifunctional Thiourea: Stereocontrolled Construction of Contiguous Quaternary and Tertiary Stereocenters
    Liao, Yu-Hua
    Chen, Wen-Bing
    Wu, Zhi-Jun
    Du, Xi-Lin
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (05) : 827 - 832
  • [36] Construction of Chiral Quaternary Carbon Centers via Asymmetric Metal Carbene gem-Dialkylation
    Dong, Shanliang
    Hong, Kemiao
    Zhang, Zhijing
    Huang, Jingjing
    Xie, Xiongda
    Yuan, Haoxuan
    Hu, Wenhao
    Xu, Xinfang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (26)
  • [37] The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis
    Hong, Allen Y.
    Stoltz, Brian M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (14) : 2745 - 2759
  • [38] Dynamic Kinetic Asymmetric Synthesis of Five Contiguous Stereogenic Centers by Sequential Organocatalytic Stetter and Michael-Aldol Reaction: Enantioselective Synthesis of Fully Substituted Cyclopentanols Bearing a Quaternary Stereocenter
    Hong, Bor-Cherng
    Dange, Nitin S.
    Hsu, Che-Sheng
    Liao, Ju-Hsiou
    Lee, Gene-Hsiang
    ORGANIC LETTERS, 2011, 13 (06) : 1338 - 1341
  • [39] Catalytic enantioselective construction of all-carbon quaternary stereocenters by an organocatalytic Diels-Alder reaction of α-substituted α, β-unsaturated aldehydes
    Kano, Taichi
    Tanaka, Youhei
    Osawa, Kenta
    Yurino, Taiga
    Maruoka, Keiji
    CHEMICAL COMMUNICATIONS, 2009, (15) : 1956 - 1958
  • [40] An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition
    Chen, Chi-Han
    Ko, Chi-Ting
    Reddy, Ganapuram Madhusudhan
    Lee, Chia-Jui
    Lin, Wenwei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5254 - 5265