Raziskava stereoselektivnih dialkilacij oksazolopiperidonskih laktamov, pridobljenih iz R-fenilglicinola in (1R, 2S)-aminoindanola

Peršolja, Peter (author), Gobec, Stanislav (mentor), Amat, Maria Mercedes (co-mentor)

Na področju asimetrične sinteze so oksazolopiperidonski laktami nedvomno odlični modeli za sintezo piperidinskih bioaktivnih spojin. Priprava omenjenih laktamov je mogoča v enem sinteznem koraku s ciklokondenzacijo delta-keto estra z enantiočistim amino alkoholom, običajno (R)-fenilglicinolom. Konformacijska togost in splošna funkcionalnost laktamov omogočata uvedbo obilice raznolikih substituentov na regio- in stereokontroliran način na mnoge položaje piperidinskega obroča.

• Language: Slovenian
• Keywords: oksazolopiperidonski laktami, R-fenilglicinol, (1R, 2S)-(+)-cis-1-amino-2-indanol, enolna alkilacija, asimetrična sinteza
• Work type: Master's thesis/paper
• Organization: FFA - Faculty of Pharmacy
• Year: 2021
• PID: 20.500.12556/RUL-131532
• Publication date in RUL: 29.09.2021

Secondary language

• Language: English
• Title: Stereoselective dialkylation studies in R-phenylglycinol- and (1R, 2S)-aminoindanol-derived oxazolopiperidone lactams

Abstract

In the field of asymmetric synthesis, oxazolopiperidone lactams are undoubtedly excellent scaffolds for the synthesis of piperidine-containing bioactive compounds. Access to these lactams is readily available in a single synthetic step by cyclocondensation reaction of a delta-keto ester with an enantiopure aminoalcohol, usually (R)-phenylglycinol. Because of their versatile functionality and conformational rigidity, it is possible to introduce substituents at different positions of the piperidine ring in a regio- and stereocontrolled manner.

• Keywords: oxazolopiperidone lactams, R-phenylglycinol, (1R, 2S)-(+)-cis-1-amino-2-indanol, enolate alkylation, asymmetric synthesis