Issue 9, 2003
From the journal:

Organic & Biomolecular Chemistry

An improved approach for the synthesis of α,α-dialkyl glycine derivatives by the Ugi–Passerini reaction†

Susana P. G. Costa,a   Hernâni L. S. Maia*a  and  Sílvia M. M. A. Pereira-Limaa  

* Corresponding authors

a Department of Chemistry, University of Minho, Gualtar, P-4710-057 Braga, Portugal
E-mail: hmaia@quimica.uminho.pt

Abstract

A general and simple strategy for routine peptide synthesis with α,α-dialkyl glycines taking advantage of the four-component Ugi–Passerini reaction is presented. The isonitrile required for the reaction can be relatively simple and its selection based on cost, as the group it generates is easily removed under acidic conditions; in addition, this removal is not visibly affected by the bulkiness of the α-alkyl groups. Being a good leaving group from the N-terminal amino group of the amino acid, 4-methoxybenzyl was the choice for the amine component of the reaction. The method is illustrated with the synthesis of a series of acyl derivatives of several α,α-dialkyl glycines. The preparation of the latter compounds is also reported.

Graphical abstract: An improved approach for the synthesis of α,α-dialkyl glycine derivatives by the Ugi–Passerini reaction

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Article information

DOI
https://doi.org/10.1039/B212473B
Article type
Paper
Submitted
16 Dec 2002
Accepted
12 Mar 2003
First published
28 Mar 2003

Org. Biomol. Chem., 2003,1, 1475-1479

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An improved approach for the synthesis of α,α-dialkyl glycine derivatives by the Ugi–Passerini reaction

S. P. G. Costa, H. L. S. Maia and S. M. M. A. Pereira-Lima, Org. Biomol. Chem., 2003, 1, 1475 DOI: 10.1039/B212473B

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