Copper and Rhodium Relay Catalysis for Selective Access to cis-2,3-Dihydroazepines

Autor:	Yingzi Li, Zongyuan Tang, Shanshan Li, Han Luo, Bao-Sheng Li, Xiaolan Xin, You Li, Luan Du
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Sulfonyl Organic Chemistry Triazole chemistry.chemical_element Alkyne Biochemistry Combinatorial chemistry Catalysis Rhodium chemistry.chemical_compound Stereospecificity chemistry Azide Physical and Theoretical Chemistry Conrotatory and disrotatory
Zdroj:	Organic Letters. 23:6450-6454
ISSN:	1523-7052 1523-7060
Popis:	A new catalytic protocol to access synthetically challenging cis-2,3-dihydroazepines is reported. The reaction starts with readily available dienals, alkynes, and sulfonyl azides as the substrates and employs copper and rhodium as relay catalysts. Key steps include a copper-catalyzed reaction between an alkyne and a sulfonyl azide to form a triazole intermediate. The subsequent activation of this triazole intermediate by a rhodium catalyst, followed by a reaction with the dienal substrate, eventually leads to the dihydroazepine product. The regio- and stereochemistries of the products are believed to be controlled through a stereospecific conrotatory 8π-electrocyclization process against a possible competing 6π-electrocyclization process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0f2364184ed8df14b80062f034f27b16 https://doi.org/10.1021/acs.orglett.1c02262 Zobrazit plný text záznamu