Gold-catalyzed cyclization of O-propargyl carbamates under mild conditions:: A convenient access to 4-alkylidene-2-oxazolidinones

被引:61
作者
Ritter, Stefanie [1 ]
Horino, Yoshikazu [1 ]
Lex, Johann [1 ]
Schmalz, Hans-Guenther [1 ]
机构
[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
关键词
oxazolidinones; heterocycles; gold catalysis; alkynes;
D O I
10.1055/s-2006-951555
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On treatment with catalytic amounts of goldi(I) chloride (AuCl) and a base co-catalyst, O-propargyl carbarnates smoothly undergo a 5-exo-dig cyclization at room temperature to afford 4-methyl ene-2-oxazolidinones in high yield. Substrates with a substituent at the alkyne terminus stereoselectively give rise to (Z)-4-alkylidene-2-oxazolidinones.
引用
收藏
页码:3309 / 3313
页数:5
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