Organoboron catalysis for direct amide/peptide bond formation

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(80), P. 11202 - 11222

Published: Jan. 1, 2024

This review explores studies on the development of direct dehydrative amide/peptide bond formation from carboxylic acids using organoboron catalysis.

Language: Английский

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Synthesis of N-methyl secondary amides via diboronic acid anhydride-catalyzed dehydrative condensation of carboxylic acids with aqueous methylamine

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: 23(10), P. 2400 - 2410

Published: Jan. 1, 2025

In this study, we present the first catalytic methodology for synthesizing N-methyl secondary amides via dehydrative condensation of hydroxycarboxylic acids with readily available and safe aqueous methylamine, employing diboronic acid anhydride (DBAA) as catalyst. DBAA catalysis can also be applied to direct amidations using ethylamine or dimethylamine. Moreover, demonstrate applicability system concise synthesis eight biologically active compounds containing β-amino alcohol motifs, including halostachine, synephrine, longimammine, phenylephrine, metanephrine, normacromerine, etilefrine, macromerine.

Language: Английский

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Backbone-Enabled and Ester Groups Switched δ-C(sp²)–H Amination/Fluorination: Cyclic Dipeptides Synthesis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5130 - 5135

Published: June 6, 2024

An efficient and concise strategy for the synthesis of cyclic dipeptides via Pd-catalyzed site-selective δ-C(sp2)–H amination/fluorination N-to-C cyclization is disclosed. The backbone amides within serves as endogenous directing groups, while desired products were switched by C-terminal ester group. This chemistry presents a novel robust alternative to construct cyclodipeptide fragments.

Language: Английский

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Enantioselective Access to Chiral 2,5-Diketopiperazines via Stereogenic-at-Cobalt(III)-Catalyzed Ugi-4CRs/Cyclization Sequences

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 16024 - 16037

Published: Nov. 2, 2023

An asymmetric synthesis of chiral 2,5-diketopiperazines by the Ugi-4CR/cyclization is exhibited. The employment catalytic anionic Co(III) complexes delivered α-propiolyl aminoamides in high yields with excellent enantioselectivities (31 examples, up to 95% ee). following treatment Ugi-adducts PPh3 leads 2,5-DKPs without significant loss (26 91%

Language: Английский

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Synthesis of Monodehydro-Diketopiperazines Enabled by Cp*Rh(III)-Catalyzed Amine-Directed N–H Functionalization

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A two-step, diversity-building sequence to prepare monodehydro-diketopiperazines from readily accessible materials is reported. Rh(III)-catalyzed, amine-directed N-H functionalization of a variety α-amino amides with diazophosphonate ester and subsequent cyclization gives phosphonate-substituted diketopiperazines. Horner-Wadsworth-Emmons reaction then provides high

Language: Английский

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Diastereoselective Spirocyclization: Entry to Spirocyclic Diketopiperazines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7822 - 7826

Published: Oct. 19, 2023

We report a novel approach to access spirocyclic compounds containing diketopiperazine (DKP) motif fused on pyrrolidine ring. The shared carbon is at the ketone oxidation state, bearing two carbon-nitrogen bonds, one of which introduced stereoselectively during cyclization event. reaction proceeds through an acid-catalyzed pendent chiral aminoamide unit onto 2,3-dehydroproline amide moiety with up >98:2 diastereoselectivity. have demonstrated generality this methodology and its applicability chemically diverse DKP-containing structures. extent stereoinduction how it varies according bulkiness substituent substrate set. This gives underexplored that may be useful in identifying new bioactive molecules.

Language: Английский

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Diboronic Acid Anhydride-Catalyzed Synthesis of Serine or Threonine Containing 2,5-Diketopiperazines

Synfacts, Journal Year: 2023, Volume and Issue: 19(08), P. 0844 - 0844

Published: July 14, 2023

Key words diboronic acid anhydride catalysis - 2,5-diketopiperazines serine threonine

Language: Английский

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