ON THE METALATION SILYLATION OF O-TRIMETHYLSILYL ALDEHYDE CYANOHYDRINS
ON THE METALATION SILYLATION OF O-TRIMETHYLSILYL ALDEHYDE CYANOHYDRINS
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DOI：
10.1021/jo00030a030
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发表时间：
1992-02-14
影响因子：
3.6
通讯作者：
KUAN, CP
中科院分区：
文献类型：
--
作者：
CUNICO, RF;KUAN, CP
用LDA和三甲基氯硅烷在-78 ℃下原位处理O-三甲基硅（饱和）醛氰醇，实现了其金属化-三甲基硅化反应。 C-甲硅烷基产物（O-三甲基甲硅烷基酰基硅烷氰醇）通常占主导地位，但在某些情况下发现N-甲硅烷基衍生物（烯酮亚胺）。 LDA可以跨后者的C = N键添加。 O-三甲基硅基苯甲醛氰醇的金属化-三甲基硅基化反应只有在每当量氰醇阴离子使用2当量三甲基氯硅烷时才能进行。
The metalation-trimethylsilyation of O-trimethylsilyl (saturated) aldehyde cyanohydrins was achieved by in situ treatment with LDA and trimethylchlorosilane at -78-degrees-C. C-Silyl products (O-trimethylsilyl acylsilane cyanohydrins) generally predominated, but N-silyl derivatives (ketenimines) were found in some instances. LDA could be added across the C = N bond of the latter. The metalation-trimethylsilylation of O-trimethylsilyl benzaldehyde cyanohydrin could only be effected if 2 equiv of trimethylchlorosilane were employed per equivalent of cyanohydrin anion.