Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence of O- Propargylic Oximes Derived from Glyoxylates

被引：11
|
作者：
Gima, Shinya [1 ]
Shiga, Keigo [1 ]
Terada, Masahiro [1 ]
Nakamura, Itaru [2 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, 6-3 Aramaki Aza Aoba, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, 6-3 Aramaki Aza Aoba, Sendai, Miyagi 9808578, Japan
来源：
SYNLETT | 2019年 / 30卷 / 04期
关键词：
gold catalysis; rearrangement; heterocycles; cyclization; progargylic oximes; isoxazolines; MOLECULAR COMPLEXITY;
D O I：
10.1055/s-0037-1611640
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We successfully extended our gold-catalyzed skeletal rearrangement reaction of O -propargylic oximes through C=N bond cleavage to include substrates having an ester group on the oxime moiety, affording the corresponding 2-isoxazolines having an alkoxycarbonylmethylene group at the 4-position in good to high yields. Our mechanistic studies indicated that the transfer of the alkoxycarbonylmethylene group proceeded in an intermolecular manner, confirming that the reaction proceeds through cyclization followed by intermolecular transfer of the alkoxycarbonylmethylene group.
引用
收藏
页码：393 / 396
页数：4
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