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Synfacts 2021; 17(10): 1129
DOI: 10.1055/s-0040-1720394
Polymer-Supported Synthesis

Zirconium Metal–Organic Framework Catalyzed Direct Amide-Bond Formation

Contributor(s):
Yasuhiro Uozumi
,
Ryoko Niimi
de Azambuja F, Loosen A, Conic D, van den Besselaar M, Harvey JN, Parac-Vogt TN. * KU Leuven, Belgium
En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts.

ACS Catal. 2021;
11: 7647-7658
DOI: 10.1021/acscatal.1c01782
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Key words

zirconium catalysis - metal–organic framework - peptides - amidation - amide bonds

Significance

The zirconium-based metal–organic framework UiO-66 promoted the dehydrative cyclization of dipeptides to form dioxopiperazines. Dipeptide molecules were treated with UiO-66 under anhydrous conditions to give the corresponding dioxopiperazines in good to excellent yields without a loss of their homochirality. The UiO-66 catalyst could be reused five times.


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Comment

Note that the intermolecular direct amide condensation of phenylacetic acid with benzylamine also took place with UiO-66 catalyst in the presence of 3 Å MS. The authors have previously reported the hydrolysis of dipeptides, a reverse counterpart of the present condensation, in the presence of UiO-66 (ACS Appl. Nano Mater. 2020, 3, 8931).


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Publication History

Article published online:
17 September 2021

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