Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Autor:	Eliott Le Du, Julien Borrel, Jerome Waser
Rok vydání:	2022
Předmět:	Hydrazines Alkynes Organic Chemistry Amino Acids Physical and Theoretical Chemistry Biochemistry Catalysis Copper
Zdroj:	Organic Letters. 24:6614-6618
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.2c02625
Popis:	We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Non-symmetrical ynehydrazides could be obtained in 25-97% yield using azaglycine derivatives as nucleophiles. The transfor-mation is compatible with most functional groups naturally occurring on amino acid side-chains and allows the transfer of silyl-, alkyl- and aryl-substituted alkynes. The obtained α-alkynyl azaglycine products could be further functionalized by nucleophilic attack or cycloaddition on the triple bond.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::07b371701b3b964ccab4f6c1b7328e54 https://doi.org/10.1021/acs.orglett.2c02625 Zobrazit plný text záznamu