Cesium Hydroxide Promoted Chemoselective N-Alkylation for the Generally Efficient Synthesis of Secondary Amines

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• 作者：Ralph N. Salvatore ; Advait S. Nagle ; Shaun E. Schmidt ; and Kyung Woon Jung
• 刊名：Organic Letters
• 出版年：1999
• 出版时间：December 16, 1999
• 年：1999
• 卷：1
• 期：12
• 页码：1893 - 1896
• 全文大小：64K
• 年卷期：v.1,no.12(December 16, 1999)
• ISSN：1523-7052

文摘

Selective N-alkylation of primary amines was developed using cesium hydroxide to prepare various secondary amines efficiently. A cesiumbase not only promoted monoalkylations of primary amines but also suppressed overalkylations. Various amines and alkyl bromides wereexamined, and the preliminary results demonstrated this methodology was highly chemoselective, favoring mono-N-alkylation over dialkylation.In particular, use of amino acid derivatives afforded the desired secondary amines exclusively.

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