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

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

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