title: Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water.
abstract: [Structure: see text] 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.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India.
authors.forename: Sunay V
authors.initials: SV
authors.lastname: Chankeshwara
authors.forename: Asit K
authors.initials: AK
authors.lastname: Chakraborti
mesh_terms: D000588:Amines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D014867:Water / Q000737:chemistry
chemical_list: D000588:Amines; D014867:Water