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Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations

Masayoshi Koshizuka, Kaito Shinoda, Kazuishi Makino and Naoyuki Shimada*

*Laboratory of Organic Chemistry for Molecular Transformations, Department of Chemistry, Institute of Natural Sciences, Nihon University, Tokyo 156-8550, Japan, Email: shimada.naoyukinihon-u.ac.jp

M. Koshizuka, K. Shinoda, K. Makino, N. Shimada, J. Org. Chem., 2023, 88, 6901-6910.

DOI: 10.1021/acs.joc.3c00195


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Abstract

Diboronic acid anhydride-catalyzed hydroxy-directed peptide bond formations enable a simple protocol for the concise synthesis of 2,5-diketopiperazines with hydroxymethyl functional groups in high yields. The sequential reactions consist of an intermolecular catalytic condensation reaction, a simple deprotection of the nitrogen-protecting group, and an intramolecular cyclization.

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proposed reaction pathway



Key Words

N-heterocycles


ID: J42-Y2023