Premium
Pyrrole‐Assisted and Easy Oxidation of Cyclic α‐Amino Acid‐ Derived Diketopiperazines under Mild Conditions
Author(s) -
Tian Hua,
Ermolenko Ludmila,
Gabant Marion,
Vergne Carine,
Moriou Céline,
Retailleau Pascal,
AlMourabit Ali
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100112
Subject(s) - diketopiperazines , chemistry , pyrrole , amino acid , organic chemistry , molecular oxygen , combinatorial chemistry , catalysis , biochemistry
A new procedure for the aerobic oxidation of α‐amino acids acylated by pyrrole‐carboxylic acid with triplet dioxygen is introduced. The reaction is general for a variety of pyrrole‐amino acid derivatives and represents a very practical and controllable method for the selective preparation of α‐hydroperoxy‐ or α‐hydroxy‐α‐amino acid diketopiperazines with molecular dioxygen. Furthermore, the non‐catalyzed direct oxidation of amino acid derivatives at the α‐position with molecular dioxygen represents a fundamental question.