A new alternative to the Mannich reaction:: Tandem radical addition-cyclization reaction for asymmetric synthesis of γ-butyrolactones and β-amino acids

被引：84
|
作者：
Miyabe, H [1 ]
Fujii, K [1 ]
Goto, T [1 ]
Naito, T [1 ]
机构：
[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 25期
关键词：
D O I：
10.1021/ol006716g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The radical addition-cyclization reaction of substrates having two different radical accepters such as acrylate and aldoxime ether moieties was studied. This new free radical mediated Mannichtype reaction proceeded smoothly via a tandem C-C bond-forming process. Furthermore, the diastereoselective tandem reaction provides the novel method for asymmetric synthesis of gamma -butyrolactones and beta -amino acid derivatives.
引用
收藏
页码：4071 / 4074
页数：4
相关论文
共 50 条
  • [31] Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic N-Sulfinyl β-Amino Ketone Ketals
    Davis, Franklin A.
    Theddu, Naresh
    Gaspari, Paul M.
    ORGANIC LETTERS, 2009, 11 (07) : 1647 - 1650
  • [32] A highly diastereoselective three-component tandem 1,4-conjugated addition-cyclization reaction to multisubstituted pyrrolidines
    Zhang, Xia
    Ji, Jingjing
    Zhu, Yingguang
    Jing, Changcheng
    Li, Ming
    Hu, Wenhao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (10) : 2133 - 2138
  • [33] Highly diastereoselective radical addition to oxime ethers:: Asymmetric synthesis of β-amino acids
    Miyabe, H
    Fujii, K
    Naito, T
    ORGANIC LETTERS, 1999, 1 (04) : 569 - 572
  • [34] Novel intermolecular carbon radical addition to a nitrone:: asymmetric synthesis of α-amino acids
    Ueda, M
    Miyabe, H
    Teramachi, M
    Miyata, O
    Naito, T
    CHEMICAL COMMUNICATIONS, 2003, (03) : 426 - 427
  • [35] Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction
    Chauhan, Pankaj
    Mahajan, Suruchi
    Kaya, Ugur
    Peuronen, Anssi
    Rissanen, Kari
    Enders, Dieter
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13): : 7050 - 7058
  • [36] Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction
    Enders, D
    Grondal, C
    Vrettou, M
    Raabe, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) : 4079 - 4083
  • [37] Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization
    Ohshima, T
    Xu, JY
    Takita, R
    Shimizu, S
    Zhong, DF
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14546 - 14547
  • [38] One-Pot Synthesis of Highly Substituted Allenylidene Derivatives via Palladium- or Nickel-Catalyzed Tandem Michael Addition-Cyclization Reaction
    Shi, Yun
    Huang, Jing
    Yang, Yan-Fang
    Wu, Lu-Yong
    Niu, Yan-Ning
    Huo, Peng-Fei
    Liu, Xue-Yuan
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 141 - 146
  • [39] ESI-MS studies on the mechanism of Pd(0)-catalyzed three-component tandem double addition-cyclization reaction
    Guo, H
    Qian, R
    Liao, YX
    Ma, SM
    Guo, YL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (37) : 13060 - 13064
  • [40] Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization
    1600, American Chemical Society (124):
12345