logo SBA

ETD

Archivio digitale delle tesi discusse presso l’Università di Pisa

Tesi etd-09192014-132728


Tipo di tesi
Tesi di laurea magistrale LM5
Autore
MARTINELLI, ELISA
URN
etd-09192014-132728
Titolo
Stereoselective synthesis of heterocyclic compounds from glycal-derived vinyl N-mesyl aziridines and oxiranes
Dipartimento
FARMACIA
Corso di studi
CHIMICA E TECNOLOGIA FARMACEUTICHE
Relatori
relatore Prof. Crotti, Paolo
relatore Dott.ssa Di Bussolo, Valeria
Parole chiave
  • N-mesyl aziridines
  • stereoselective synthesis
  • vinyl oxiranes
Data inizio appello
08/10/2014
Consultabilità
Tesi non consultabile
Data di rilascio
08/10/2084
Riassunto
Multisubstituted 2,5-dihydropyrroles and 2,5-dihydrofurans are recognized as valuable heterocyclic systems because they could be advantageously used as starting materials for the preparation of many pharmaceutically relevant compounds. The possibility of the construction of an enantiomerically pure cis-2,5-disubstituted-2,5-dihydropyrrole and cis-2,5disubstituted-2,5-dihydrofuran systems respectively starting from glycal-derived vinyl N-mesyl aziridines and oxiranes, when subjected to appropriate reaction conditions, was examined.
The reaction of N-mesyl aziridines and oxiranes with metal enolates derived from active methylene compounds afforded, through a rearrangement process implying an opening-closing process with contemporary ring contraction of the initially obtained 1,4-addition product (primary reaction product), the corresponding cis-2,5-disubstituted-2,5-dihydropyrrole and cis-2,5-disubstituted-2,5-dihydrofuran (both secondary reaction products), respectively, in a completely region- and stereoselective fashion.
File