Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines

Chankeshwara, Sunay V. ; Chakraborti, Asit K. (2006) Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines Synthesis, 2006 (16). pp. 2784-2788. ISSN 0039-7881

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Official URL: https://www.thieme-connect.de/DOI/DOI?10.1055/s-20...

Related URL: http://dx.doi.org/10.1055/s-2006-942492

Abstract

Indium(III) bromide and chloride efficiently catalysed the N-tert-butoxycarbonylation of amines with (Boc)2O at room temperature and under solvent-free conditions. Various aromatic, heteroaromatic and aliphatic amines were converted to N-tert-butylcarbamates in excellent yields in short times. Chiral amines, esters of α-amino acids and β-amino alcohols afforded optically pure N-t-Boc derivatives in high yields. The reactions were chemoselective and no competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation were observed. Chemoselective conversion to N-tert-butylcarbamates took place with amino alcohols without any formation of oxazolidinones.

Item Type:Article
Source:Copyright of this article belongs to Thieme Publishing.
Keywords:Indium(III) Halides; N-Tert-Butylcarbamates; Amines; Chiral α-Amino Acid Esters; Di-Tert-Butyl Dicarbonate; Chemoselectivity Solvent-Free; Room Temperature
ID Code:100437
Deposited On:20 Jan 2017 04:49
Last Modified:20 Jan 2017 04:49

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