SILVER(I)-CATALYZED AMINOCYCLIZATION OF 2,3-BUTADIENYL AND 3,4-PENTADIENYL CARBAMATES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 4-VINYL-2-OXAZOLIDINONES AND 4-VINYLTETRAHYDRO-2H-1,3-OXAZIN-2-ONES

被引：36

作者：

KIMURA, M ^{[1
]}

TANAKA, S ^{[1
]}

TAMARU, Y ^{[1
]}

机构：

[1] NAGASAKI UNIV, FAC ENGN, DEPT APPL CHEM, NAGASAKI 852, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 06期

关键词：

D O I：

10.1246/bcsj.68.1689

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates 1 (benzene, 50 degrees C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C-5-Me to >30 for C-5-phenyl, isopropenyl, and t-butyl derivatives. 3,4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one 4 in synthetically useful yields and in higher trans selectivities than 1.

引用

页码：1689 / 1705

页数：17

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