Síntesis enantioselectiva de oxazolidinonas mediante resolución cinética con catalizadores tipo amidina

Fernández-Llamazares Aragón, Emma

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TITLE:

Síntesis enantioselectiva de oxazolidinonas mediante resolución cinética con catalizadores tipo amidina - TFG:2551

Handle:

https://hdl.handle.net/20.500.11797/TFG2551

Student:	Fernández-Llamazares Aragón, Emma
Language:	spa
Title in original language:	Síntesis enantioselectiva de oxazolidinonas mediante resolución cinética con catalizadores tipo amidina
Title in different languages:	Enantioselective synthesis of oxazolidinones: Amidine-based catalytic kinetic resolution
Keywords:	oxazolidinone, kinetic resolution, enantioselective
Subject:	Química
Abstract:	The present project aims at developing new methodologies for the synthesis of enantioenriched sphingosine analogues. The proposed retrosynthetic pathway involved a sequential aziridination/ring-opening of dienyl carbamates followed by an organocatalysed kinetic resolution (KR) of the so obtained racemic oxazolidinones. Previous optimisation of the KR has demonstrated the key role of the exocyclic hydroxy protecting group, with the highest enantiocontrol obtained for benzoylated starting material due to cation-π interactions with the catalyst. In order to improve KR results, three different substrates bearing more electron-rich carbonyl groups such as carbonate and carbamate moieties were synthesised and subsequently tested. Thus, benzyl carbonate and diisopropyl carbamate rendered enantioenriched products in high selectivities similar to those obtained for benzoyl group whereas isopropyl carbonate proved to be slightly less effective.
Project director:	Castillón Miranda, Sergio
Work's codirector:	Díaz Giménez, M. Yolanda
Department:	Química Analítica i Química Orgànica
Education area(s):	Química
Entity:	Universitat Rovira i Virgili (URV)
TFG credits:	12
Creation date in repository:	2020-02-28
Work's public defense date:	2019-06-13
Academic year:	2018-2019
Confidenciality:	No
Subject areas:	Chemistry
Access rights:	info:eu-repo/semantics/openAccess

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Type:	info:eu-repo/semantics/bachelorThesis
Títol:	Síntesis enantioselectiva de oxazolidinonas mediante resolución cinética con catalizadores tipo amidina
Contributor:	Díaz Giménez, M. Yolanda Castillón Miranda, Sergio
Subject:	Química Chemistry Química Química
Date:	2019-06-13
Language:	spa
Creator:	Fernández-Llamazares Aragón, Emma
Rights:	info:eu-repo/semantics/openAccess

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