Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones

被引：18
|
作者：
Bournaud, Chloee [1 ]
Marchal, Estelle [1 ]
Quintard, Adrien [1 ]
Sulzer-Mosse, Sarah [1 ]
Alexakis, Alexandre [1 ]
机构：
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland
来源：
TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 13-14期
关键词：
CONJUGATE ADDITION; DIASTEREOSELECTIVE SYNTHESIS; KETONES; ACIDS; ETHERS;
D O I：
10.1016/j.tetasy.2010.03.043
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1666 / 1673
页数：8
相关论文
共 50 条
  • [21] 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
  • [22] Catalytic enantioselective addition of diorganozinc reagents to vinyl sulfones
    Desrosiers, Jean-Nicolas
    Bechara, William S.
    Charette, Andre B.
    ORGANIC LETTERS, 2008, 10 (11) : 2315 - 2318
  • [23] Enantioselective synthesis of β-amino sulfones by aza-Michael addition to alkenyl sulfones
    Enders, D
    Müller, SE
    Raabe, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (1-2) : 195 - 197
  • [24] Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction
    Hayashi, Y
    Gotoh, H
    Tamura, T
    Yamaguchi, H
    Masui, R
    Shoji, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16028 - 16029
  • [25] An efficient, asymmetric organocatalyst-mediated conjugate addition of nitroalkanes to unsaturated cyclic and acyclic ketones
    Mitchell, CET
    Brenner, SE
    García-Fortanet, J
    Ley, SV
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (10) : 2039 - 2049
  • [26] Highly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins
    Guo, Xing-Tao
    Sha, Feng
    Wu, Xin-Yan
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (07) : 6373 - 6380
  • [27] Enantioselective Organocatalytic Michael Addition of Aldehydes to Trifluoroethylidene Malonates
    Wen, Lele
    Shen, Qilong
    Lu, Long
    ORGANIC LETTERS, 2010, 12 (20) : 4655 - 4657
  • [28] Highly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins
    Xing-Tao Guo
    Feng Sha
    Xin-Yan Wu
    Research on Chemical Intermediates, 2016, 42 : 6373 - 6380
  • [29] Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes
    Wu, Shanchao
    Li, Yu
    Zhang, Yongqiang
    Fang, Kun
    Dong, Guoqiang
    Liu, Na
    Miao, Zhenyuan
    Yao, Jianzhong
    Wang, Wei
    Zhang, Wannian
    Sheng, Chunquan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (16) : 3926 - 3933
  • [30] 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
12345