Banca de DEFESA: NAIRA VIEIRA MACHADO

Uma banca de DEFESA de MESTRADO foi cadastrada pelo programa.
DISCENTE : NAIRA VIEIRA MACHADO
DATA : 07/02/2020
HORA: 14:00
LOCAL: Campus Santo André
TÍTULO:

ENANTIOSELECTIVE REDUCTION OF HETEROCYCLIC PROHIRAL KETONES CATALYZED BY CARROT

PÁGINAS: 85
GRANDE ÁREA: Ciências Exatas e da Terra
ÁREA: Química
SUBÁREA: Química Orgânica
ESPECIALIDADE: Síntese Orgânica
RESUMO:

This work presents the reduction of ketones considered in the literature as “difficult to reduce” asymmetrically. These ketones are called this way because they contain α and α' groups of the carbonyl group with low structural differences, making it difficult to obtain enantiomerically pure products. In this case, the ketones selected for reduction were: 1-Z-3-pyrrolidinone, dihydro-2-methyl-3 (2H) -furanone, dihydro-3 (2H) -thiophenone, 1-Boc-3-pyrrolidinone and 1 -benzyl-3-pyrrolidinone. Chiral alcohols from these ketones are important because of their use in the synthesis of bioactive compounds. For this purpose, the carrot is a well-known biocatalyst for reduction reactions with prochiral ketones to obtain alcohols with high conversion values and enantiomeric excess. Lipases, in turn, are biocatalysts used in enzymatic resolutions of racemic alcohols because they are selective, affordable and with industrial application. The best methodology between ketone bioreduction against enzymatic kinetic resolution will be evaluated. The results of ketone reductions, with the exception of 1-benzyl-3-pyrrolidinone, using carrot pieces were applicable in reducing ketones considered difficult to reduce. Regarding the enzymatic kinetic resolution of racemic alcohol 1-Boc-3-pyrrolidinol, Amano PS, PS-IM and PCL lipases presented the best results of enantiomeric excesses. However, enzymatic kinetic resolutions are considered better in larger-scale reactions. The reduction of carrot-catalyzed ketones offers high convention values and enantiomeric excess.

 

MEMBROS DA BANCA:
Presidente - Interno ao Programa - 1600860 - ALVARO TAKEO OMORI
Membro Titular - Examinador(a) Interno ao Programa - 1544379 - ANDERSON ORZARI RIBEIRO
Membro Titular - Examinador(a) Externo à Instituição - CINTIA DUARTE DE FREITAS MILAGRE - UNESP
Membro Suplente - Examinador(a) Interno ao Programa - 1544344 - VANI XAVIER DE OLIVEIRA JUNIOR
Membro Suplente - Examinador(a) Externo ao Programa - 3146362 - SUMBAL SABA