Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of O-Propioloyl Oximes

被引：43

作者：

Nakamura, Itaru ^{[1
,2
]}

Okamoto, Masashi ^{[2
]}

Terada, Masahiro ^{[2
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

关键词：

C-N BOND; ORGANIC TRANSFORMATIONS; CYCLOISOMERIZATION; ENYNES; PLATINUM; ALKYNES; REARRANGEMENT; CONSTRUCTION; HETEROCYCLES; ACTIVATION;

D O I：

10.1021/ol100581m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 degrees C in the presence of Au(PPh(3))NTf(2) (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.

引用

页码：2453 / 2455

页数：3

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