Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction

被引:198
|
作者
Hayashi, Y [1 ]
Gotoh, H [1 ]
Tamura, T [1 ]
Yamaguchi, H [1 ]
Masui, R [1 ]
Shoji, M [1 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
D O I
10.1021/ja055740s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities. Copyright © 2005 American Chemical Society.
引用
收藏
页码:16028 / 16029
页数:2
相关论文
共 50 条
  • [41] Highly Enantioselective Michael Addition of Ketones to Nitroolefins with a Pyrrolidine-Based Phthalimide as an Enamine-Type Organocatalyst
    Ban, Shu-rong
    Xie, Hong-yu
    Zhu, Xi-xia
    Li, Qing-shan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (32) : 6413 - 6417
  • [42] Efficient and Highly Enantioselective Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Surfactant-type Organocatalyst in the Presence of Water
    Hu, Feng
    Guo, Chang-Shan
    Xie, Jin
    Zhu, Hai-Liang
    Huang, Zhi-Zhen
    CHEMISTRY LETTERS, 2010, 39 (04) : 412 - 414
  • [43] AN ENANTIOSELECTIVE CONSTRUCTION OF PYRROLIDONES BEARING FUNCTIONALIZED APPENDAGES VIA AN ASYMMETRIC INTRAMOLECULAR MICHAEL REACTION
    HIRAI, Y
    TERADA, T
    KATOH, H
    SONOHARA, S
    MOMOSE, T
    HETEROCYCLES, 1991, 32 (01) : 7 - 10
  • [44] Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes
    Parhi, Biswajit
    Gurjar, Jitendra
    Pramanik, Suman
    Midya, Abhisek
    Ghorai, Prasanta
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4654 - 4663
  • [45] Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction
    Faisca Phillips, Ana Maria
    Barros, Maria Teresa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (01) : 152 - 163
  • [46] Polystyrene supported benzoylthiourea-pyrrolidine organocatalyst for the enantioselective Michael addition
    Androvic, Ladislav
    Drabina, Pavel
    Svobodova, Marketa
    Sedlak, Milos
    TETRAHEDRON-ASYMMETRY, 2016, 27 (16) : 782 - 787
  • [47] Enantioselective Michael additions of aldehydes to nitroalkenes catalyzed with ionically tagged organocatalyst
    Sebesta, Radovan
    Latika, Attila
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2014, 12 (03): : 416 - 425
  • [48] Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst
    Izzo, Joseph A.
    Myshchuk, Yaroslaw
    Hirschi, Jennifer S.
    Vetticatt, Mathew J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (16) : 3934 - 3939
  • [49] The smallest organocatalyst in highly enantioselective direct aldol reaction in wet solvent-free conditions
    Bhowmick, Sudipto
    Kunte, Sunita S.
    Bhowmick, Kartick C.
    RSC ADVANCES, 2014, 4 (46) : 24311 - 24315
  • [50] Half-sandwich complexes of rhodium containing cysteine-derived ligands
    Carmona, Maria
    Rodriguez, Ricardo
    Lahoz, Fernando J.
    Garcia-Orduna, Pilar
    Osante, Inaki
    Cativiela, Carlos
    Lopez, Jose A.
    Carmona, Daniel
    DALTON TRANSACTIONS, 2016, 45 (36) : 14203 - 14215