Stereocontrolled access to enantiopure to enantiopure 7-substituted cis- and trans-octahydroindoles

Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2- oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted o...

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Detalles Bibliográficos
Autores: Ghirardi, Elena, Griera Farres, Rosa, Piccichè, Miriam, Molins i Grau, Elies, Fernández Cadenas, Israel, Bosch Cartes, Joan, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/108046
Acceso en línea:https://hdl.handle.net/2445/108046
Access Level:acceso abierto
Palabra clave:Lactames
Síntesi asimètrica
Lactams
Asymmetric synthesis
Descripción
Sumario:Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2- oxocyclohexaneacetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted octahydroindoles with a variety of stereochemical patterns have been developed. The methodology has been successfully applied to the synthesis of (+)-α-lycorane.