Formation of the lithium enolate of N,N-dimethyl-2-trimethylsilylacetamide. Reaction with carbonyl compounds and epoxides
Formation of the lithium enolate of N,N-dimethyl-2-trimethylsilylacetamide. Reaction with carbonyl compounds and epoxides
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DOI：
10.1021/jo00404a020
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发表时间：
1978-05
影响因子：
3.6
通讯作者：
R. Woodbury;M. Rathke
中科院分区：
文献类型：
--
作者：
R. Woodbury;M. Rathke
添加A，。N-二甲基-2-三甲基甲硅烷基乙酰胺与二异丙基氨基锂或正丁基锂生成烯醇化锂4，其分离为白色固体。烯醇化物在25 ℃的THF溶液中可稳定数天。烯醇化物与醛或酮反应得到α-不饱和酰胺。烯酯与环氧化物反应，得到相应的加成产物，然后是三甲基硅烷基从碳氧上的1，4迁移。
Addition of A,. ZV-dimethyl-2-trimethylsilylacetamide to either lithium diisopropylamide or n-butyllithium gen-erates the lithium enolate 4, which was isolated as a white solid. The enolate is stable for several days in THF solu-tion at 25 C. Reaction of the enolate with aldehydes or ketones gives, ß-unsaturated amides. Reaction of the eno-late with epoxides gives products corresponding to addition followed by 1, 4 migration of the trimethylsilyl grouping from carbonto oxygen.