Catalyse intramoleculaire de l'aminolyse d'heterocycles phosphores derives des α aminoamides. I: Synthese de (thio) phosphor(N)diamides incorporant un residu de ss aminoacide

Article abstract of DOI:10.1080/10426509808545466

A general scheme of intramolecular nucleophilic catalysis of aminolysis of the heterocycles B is proposed (Figure 2). The requisite heterocycle D, when built with a β aminoamide residue, allows also a repetitive β peptide synthesis, as with α aminoacids (Figure 1). In order to evaluate the feasibility of both schemes, fifteen phosphor(n)diamides (table III) incorporating one residue of β aminoacid, in form of esters 3, acids 5 (models of E, Figure 2), nitrile 11, or hydrazides 12 have been synthesized starting from P(IV) dichlorides 1 (Figure 3). Unexpectedly hydrolysis of nitriles 6 b c leads to β diacids 9 b c with the regular acids 8 b c.

Full text of DOI:10.1080/10426509808545466

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Phosphorus, Sulfur, and
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Catalyse Intramoleculaire
De L'Aminolyse
D'Heterocycles
Phosphores Derives
Des α Aminoamides.
I: Synthese De (Thio)
Phosphor(N)Diamides
Incorporant Un Residu De
ß Aminoacide
Frederic Dujols , Philippe Jollet & Michel
Mulliez
a Laboratoire Interactions Moléculaires et
Réactivité Chimique et Photochimique, UMR
CNRS n° 5623 Université Paul Sabatier , 118
Route de Narbonne, 31062 Toulouse Cedex
04, (France)
b Laboratoire Interactions Moléculaires et
Réactivité Chimique et Photochimique, UMR
CNRS n° 5623 Université Paul Sabatier , 118
Route de Narbonne, 31062 Toulouse Cedex
04, (France)
c Laboratoire Interactions Moléculaires et
Réactivité Chimique et Photochimique, UMR
CNRS n° 5623 Université Paul Sabatier , 118

Route de Narbonne, 31062 Toulouse Cedex
04, (France)
Published online: 17 Mar 2008.
To cite this article: Frederic Dujols , Philippe Jollet & Michel Mulliez (1998)
Catalyse Intramoleculaire De L'Aminolyse D'Heterocycles Phosphores Derives
Des α Aminoamides. I: Synthese De (Thio) Phosphor(N)Diamides Incorporant
Un Residu De ß Aminoacide, Phosphorus, Sulfur, and Silicon and the Related
Elements, 134:1, 231-254, DOI: 10.1080/10426509808545466
To link to this article: http://dx.doi.org/10.1080/10426509808545466
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