EFFICIENT SYNTHESIS OF 2-VINYL-GAMMA-BUTYROLACTONES AND 2-VINYL-GAMMA-BUTYROLACTAMS BY PALLADIUM-CATALYZED DECARBOXYLATIVE CARBONYLATION

被引：26
|
作者：
BANDO, T
TANAKA, S
FUGAMI, K
YOSHIDA, Z
TAMARU, Y
机构：
[1] NAGASAKI UNIV, FAC ENGN, DEPT APPL CHEM, NAGASAKI 852, JAPAN
[2] KYOTO UNIV, FAC ENGN, DEPT SYNTHET CHEM, KYOTO 606, JAPAN
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 01期
关键词：
D O I：
10.1246/bcsj.65.97
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
4-Vinyl-1,3-dioxan-2-ones (cyclic carbonates) undergo decarboxylation-carbonylation by the catalysis of Pd(0) species under CO (in most cases, 1 atm) to provide 2-vinyl-gamma-butyrolactones in good yields. The course of the reaction of 6-vinyltetrahydro-2H-1,3-oxazin-2-ones (cyclic carbamates) depends on the substituent on the nitrogen atom. When it is H or Ts (and COPh), 2-vinyl-gamma-butyrolactams or 6-amino-3-hexenoic acid esters are obtained. Cyclic N-benzylcarbamates are unreactive. trans-2,3-Disubstituted lactones and lactams arise stereoselectively from carbonates and carbamates, irrespective of their stereochemistry, respectively.
引用
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页码：97 / 110
页数：14
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