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

Chankeshwara, Sunay V. ; Chakraborti, Asit K. (2006) Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water Organic Letters, 8 (15). pp. 3259-3262. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol0611191

Related URL: http://dx.doi.org/10.1021/ol0611191

Abstract

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 α-amino acids, and β-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.

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ID Code:100439
Deposited On:19 Jan 2017 12:39
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