期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 67, 期 3, 页码 674-683出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo010643c
关键词
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资金
- NIGMS NIH HHS [R01 GM62767] Funding Source: Medline
A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.
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