Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water

被引：188

作者：

Chankeshwara, Sunay V. ^{[1
]}

Chakraborti, Asit K. ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Natl Inst Pharmaceut Educ & Res, Nagar 160062, Pubjab, India

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

D O I：

10.1021/ol0611191

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalyst-free N-tert-butyloxycarbonylation of amines in water is reported. The N-t-Boc derivatives were formed chemoselectively without any isocyanate, urea, N, N-di-t-Boc, and O/S-t-Boc as side products. Chiral amines, esters of alpha-amino acids, and beta-amino alcohol afforded optically pure N-t-Boc derivatives. Amino alcohol and 2-aminophenol afforded the N-t-Boc derivative without oxazolidinone formation. Selectivity was observed during competition of aromatic amine vs aliphatic amine, amine vs amino acid ester, amine vs amino alcohol, and primary amine vs secondary amine.

引用

页码：3259 / 3262

页数：4

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