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
  • [1] Highly, diastereo- and enantioselective aziridination of α β-unsaturated amides with diaziridine and mechanistic consideration on its stereochemistry
    Ishihara, H
    Hori, K
    Sugihara, H
    Ito, YN
    Katsuki, T
    HELVETICA CHIMICA ACTA, 2002, 85 (12) : 4272 - 4286
  • [2] cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine
    Hori, K
    Sugihara, H
    Ito, YN
    Katsuki, T
    TETRAHEDRON LETTERS, 1999, 40 (28) : 5207 - 5210
  • [3] K-10 catalyzed highly diastereoselective aziridination of imines
    Carlson, Alena
    Borkin, Dmitry
    Torok, Bela
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [4] Highly diastereoselective synthesis of β-hydroxy amides from β-keto amides
    Bartoli, G
    Bosco, M
    Marcantoni, E
    Massaccesi, M
    Rinaldi, S
    Sambri, L
    SYNTHESIS-STUTTGART, 2004, (18): : 3092 - 3096
  • [5] Highly Stereoselective Halocyclopropanation of α,β-Unsaturated Amides
    Concellon, Jose M.
    Rodriguez-Solla, Humberto
    Blanco, Elena G.
    Villa-Garcia, Maria A.
    Alvaredo, Noemi
    Garcia-Granda, Santiago
    Rosario Diaz, M.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (13) : 2185 - 2198
  • [6] Highly diastereoselective epoxidation of α,β-unsaturated carbonyl compounds using sodium peroxide
    Reddy, VK
    Haritha, B
    Yamashita, M
    LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (02) : 128 - 131
  • [7] Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams
    Byrd, Katherine M.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 530 - 562
  • [8] Aziridination of α,β-unsaturated ketones
    Fioravanti, S
    Pellacani, L
    Tabanella, S
    Tardella, PA
    TETRAHEDRON, 1998, 54 (46) : 14105 - 14112
  • [9] Highly diastereoselective reduction of γ-keto amides:: Diastereoselective synthesis of γ-butyrolactones with contiguous chiral centers
    Satoh, M
    Washida, S
    Takeuchi, S
    Asaoka, M
    HETEROCYCLES, 2000, 52 (01) : 227 - 236
  • [10] Highly diastereoselective additions of methoxyallene and acetylenes to chiral α-keto amides
    Youn, SW
    Kim, YH
    Hwang, JW
    Do, Y
    CHEMICAL COMMUNICATIONS, 2001, (11) : 996 - 997
12345