Issue 22, 2024

Recent advances in asymmetric synthesis of chiral amides and peptides: racemization-free coupling reagents

Abstract

Over past decades, chiral amides and peptides have emerged as powerful and versatile compounds due to their various biological activities and interesting molecular architectures. Although some chiral condensation reagents have been applied successfully for their synthesis, the introduction of racemization-free methods of amino acid activation have shown lots of advantages in terms of their low cost and low toxicity. In this review, advancements in amide and peptide synthesis using racemization-free coupling reagents over the last 10 years are summarized. Various racemization-free coupling reagents have been applied in the synthesis of enantioselective amides and peptides, including ynamides, allenones, HSi[OCH(CF3)2]3, Ta(OMe)5, Nb(OEt)5, Ta(OEt)5, TCFH-NMI, water-removable ynamides, DBAA, DATB, o-NosylOXY, TCBOXY, Boc-Oxyma, NDTP, 9-silafluorenyl dichlorides, the Mukaiyama reagent, EDC and T3P. The racemization-free reagents described in this review provide an alternative greener option for the asymmetric synthesis of chiral amides and peptides. We hope that this review will inspire further studies and developments in this field.

Graphical abstract: Recent advances in asymmetric synthesis of chiral amides and peptides: racemization-free coupling reagents

Article information

Article type
Review Article
Submitted
06 Apr 2024
Accepted
09 May 2024
First published
10 May 2024

Org. Biomol. Chem., 2024,22, 4420-4435

Recent advances in asymmetric synthesis of chiral amides and peptides: racemization-free coupling reagents

Y. Guo, M. Wang, Y. Gao and G. Liu, Org. Biomol. Chem., 2024, 22, 4420 DOI: 10.1039/D4OB00563E

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