Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

Autor:	Goyeong Choi, Yonguk Jeong, Jong-Wha Jung, Seoyoung Jo, Juyeon Mun, Seok-Ho Kim
Jazyk:	angličtina
Rok vydání:	2019
Předmět:	Molecular Structure Chemistry aza-quaternary carbon center Organic Chemistry rearrangement Pharmaceutical Science Stereoisomerism Key features Medicinal chemistry Article Carbon Analytical Chemistry Allyl Compounds ring expansion Chemistry (miscellaneous) Drug Discovery Molecular Medicine Stereoselectivity Physical and Theoretical Chemistry Quaternary carbon
Zdroj:	Molecules Volume 24 Issue 24
ISSN:	1420-3049
Popis:	The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and acyclic substrates underwent the unexpected rearrangement to afford products in moderate to high yields, and (4) the reaction seemed to be highly stereoselective. In addition, a plausible mechanism has been discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::af9127c611967ba9dffa4379bbe02f4f http://europepmc.org/articles/PMC6943665 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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