Conjugate systems in the construction of heterocycles and quaternary stereocenters

Autor:	Adriana Benavides, Rafael Bautista, Pablo Bernal, Fabiola Jiménez, Carlos González-Romero, Aydeé Fuentes-Benites, María del Carmen Cruz, Joaquín Tamariz
Rok vydání:	2007
Předmět:	chemistry.chemical_compound Enantiopure drug Nucleophile Chemistry General Chemical Engineering Intramolecular force Synthon Organic chemistry Regioselectivity Total synthesis General Chemistry Isocyanate Stereocenter
Zdroj:	Pure and Applied Chemistry. 79:181-191
ISSN:	1365-3075 0033-4545
Popis:	The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good stereoisomeric ratios. The novel approach for the synthesis of benzofurans and indoles by intramolecular cyclization of enaminones has been applied in the preparation of furobenzofurans starting from benzo-bis-enaminones.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c1ca1d47ecdefdea610e4bdbc9a23eaf https://doi.org/10.1351/pac200779020181 Zobrazit plný text záznamu