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JOURNALS // Uspekhi Khimii // Archive

Usp. Khim., 2019 Volume 88, Issue 3, Pages 248–279 (Mi rcr4245)

This article is cited in 10 papers

Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds

D. P. Zarezin, V. G. Nenajdenko

Lomonosov Moscow State University, Faculty of Chemistry

Abstract: This review deals with applications of chiral $\alpha$-amino diazoketones, $\alpha$-amino acid derivatives, in the synthesis of various biologically active compounds. General approaches to the synthesis of chiral $\alpha$-amino diazoketones, including the Arndt–Eistert reaction, acylation of trimethylsilyldiazomethanes, etc., are discussed. Due to the presence of three functional groups, these building blocks can be used to produce a wide range of organic compounds with potential physiological activity, ranging from various heterocyclic compounds to peptidomimetics. Methods for the synthesis of $\beta$-amino acid-containing peptides and depsipeptides, amino acid derivatives and heterocyclic compounds with three- to seven-membered rings are considered.
The bibliography includes 226 references.

Keywords: aminodiazoketones, peptides, depsipeptides, lactams.

Received: 02.07.2018

DOI: 10.1070/RCR4852


 English version:
Russian Chemical Reviews, 2019, 88:3, 248–279

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