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Synfacts 2020; 16(05): 0605
DOI: 10.1055/s-0040-1707597
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Zinc-Catalyzed Peptide Synthesis by Using a Nicotinate-Directed Protocol

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Hollanders K, Renders E, Gadais C, Masullo D, Van Raemdonck L, Wybon CC. D, Martin C, Herrebout WA, Maes BU. W. * Ballet S. * Vrije Universiteit Brussel and University of Antwerp, Belgium
Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis.

ACS Catal. 2020;
10: 4280-4289
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Publication History

Publication Date:
20 April 2020 (online)

 
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Key words

zinc catalysis - palladium catalysis - butylnicotinate amino amides - directing group - transamidation

Significance

Development of new systems for peptide-bond formation is an ongoing challenge to organic chemists. The authors report a new strategy using tert-butyl nicotinate amino amides, formed from amino acids and tert-butyl 2-chloro­nicotinate with palladium catalysis, as excellent ­nucleophiles for the synthesis of dipeptides.


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Comment

Various tert-butyl nicotinate amino amides were smoothly generated in high yields and high enantioselectivities. The products and amino acid ester HCl salts were easily converted into the corresponding dipeptides by using zinc catalysis. Furthermore, this protocol can also be applied in the synthesis of tripeptides.


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