Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

被引：0
|
作者：
Ishihara, H [1 ]
Ito, YN [1 ]
Katsuki, T [1 ]
机构：
[1] Kyushu Univ, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan
来源：
CHEMISTRY LETTERS | 2001年 / 10期
关键词：
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with alpha,beta -unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.
引用
收藏
页码：984 / 985
页数：2
相关论文
共 50 条
  • [41] Carbamoyl Anion Addition to N-Sulfinyl Imines: Highly Diastereoselective Synthesis of α-Amino Amides
    Reeves, Jonathan T.
    Tan, Zhulin
    Herbage, Melissa A.
    Han, Zhengxu S.
    Marsini, Maurice A.
    Li, Zhibin
    Li, Guisheng
    Xu, Yibo
    Fandrick, Keith R.
    Gonnella, Nina C.
    Campbell, Scot
    Ma, Shengli
    Grinberg, Nelu
    Lee, Heewon
    Lu, Bruce Z.
    Senanayake, Chris H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (15) : 5565 - 5568
  • [42] Dual Activation of Unsaturated Amides with Schwartz's Reagent: A Diastereoselective Access to Cyclopentanols and N,O-Dimethylcyclopentylhydroxylamines.
    Coelho, Aurelien
    Zafindrajaona, Mahasoa-Salina Souvenir
    Vallee, Alexis
    Behr, Jean-Bernard
    Vasse, Jean-Luc
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (03)
  • [43] Diastereoselective synthesis of α,β-unsaturated systems
    Castelani, P
    Comasseto, JV
    TETRAHEDRON, 2005, 61 (09) : 2319 - 2326
  • [44] Catalytic asymmetric aziridination of a, b- unsaturated aldehydes
    Deiana, Luca
    Cordova, Armando
    Dziedzic, Pawel
    Zhao, Gui-Ling
    Vesely, Jan
    Ibrahem, Ismail
    Rios, Ramon
    Sun, Junliang
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [45] Facile synthesis of novel spiroheterocycles via diastereoselective aziridination of cyclic enones
    Yang, Kai-Chuan
    Li, Jun-Long
    Shen, Xu-Dong
    Li, Qiang
    Leng, Hai-Jun
    Huang, Qian
    Zheng, Peng-Kun
    Gou, Xiao-Jun
    Zhi, Yong-Gang
    RSC ADVANCES, 2017, 7 (34): : 21175 - 21179
  • [46] Highly Enantio- and Diastereoselective Synthesis of 1,2,3-Trisubstituted Cyclopropanes from α,β-Unsaturated Amides and Stabilized Sulfur Ylides Catalyzed by a Chiral Copper(I) Complex
    Pagire, Santosh K.
    Kumagai, Naoya
    Shibasaki, Masakatsu
    ACS CATALYSIS, 2021, 11 (18) : 11597 - 11606
  • [47] Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy
    Gerstner, Nels C.
    Adams, Christopher S.
    Grigg, R. David
    Tretbar, Maik
    Rigoli, Jared W.
    Schomaker, Jennifer M.
    ORGANIC LETTERS, 2016, 18 (02) : 284 - 287
  • [48] HIGHLY ANTI-DIASTEREOSELECTIVE REDUCTION OF 2-ALKYL-3-OXO AMIDES BY POTASSIUM TRIETHYLBOROHYDRIDE
    ITO, Y
    KATSUKI, T
    YAMAGUCHI, M
    TETRAHEDRON LETTERS, 1985, 26 (38) : 4643 - 4646
  • [49] Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles
    Gietter-Burch, Amber A. S.
    Mitrut, Roxana E.
    Watson, Donald A.
    ORGANIC LETTERS, 2015, 17 (21) : 5468 - 5471
  • [50] Electrophilic cyclization of unsaturated amides
    Robin, S
    Rousseau, G
    TETRAHEDRON, 1998, 54 (45) : 13681 - 13736
12345