ChemInform Abstract: 2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates

Autor:	Varun Kumar, Aigars Jirgensons, Kristine Klimovica, Dace Rasina
Rok vydání:	2015
Předmět:	Carbenium ion chemistry.chemical_compound Allylic rearrangement chemistry 2-vinyl threoninol Acid catalyzed Substitution (logic) Stereoselectivity General Medicine Threonine Medicinal chemistry Stereocenter
Zdroj:	ChemInform. 46
ISSN:	0931-7597
DOI:	10.1002/chin.201543139
Popis:	A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C–N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::96482433e9c9b67dd6016b458333461f https://doi.org/10.1002/chin.201543139 Zobrazit plný text záznamu Plný text