NHC-Catalyzed Aza-Benzoin Condensation of N,N′-Dipyridin-2-yl Aminals with Aldehydes

Autor:	Ryo Takashima, Yumiko Suzuki, Justin S. Lamb
Rok vydání:	2021
Předmět:	Direct route Chemistry Organic Chemistry Organic chemistry Benzoin condensation Catalysis
Zdroj:	The Journal of Organic Chemistry. 86:10224-10234
ISSN:	1520-6904 0022-3263
Popis:	α-Amino ketones are useful compounds because of their synthetic utility and bioactivities. After observing the ability of N,N'-dipyridin-2-yl aminals to form imines in situ, the synthesis of α-amino ketones using N,N'-dipyridin-2-yl aminals was proposed. Through the NHC-catalyzed aza-benzoin reaction between aromatic/aliphatic aldehydes and N,N'-dipyridin-2-yl aminals, α-amino ketones, including aromatic, heterocyclic, and aliphatic versions, were synthesized with yields up to 99%. A direct route toward N-Boc-protected α-amino ketones from N,N,N'-tris-Boc aminals was also discovered, yielding the desired N-Boc-protected α-amino ketones in yields up to 73%.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1d5d01175ee595cb49a592ebe2cd8ceb https://doi.org/10.1021/acs.joc.1c00973 Zobrazit plný text záznamu