NAGIOS: RODERIC FUNCIONANDO

Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones

Repositori DSpace/Manakin

Valencià Castellano

Inici
Investigació
e-prints
23 - Química
Visualitza element

IMPORTANT: Aquest repositori està en una versió antiga des del 3/12/2023. La nova instal.lació está en https://roderic.uv.es/

Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones

Mostra el registre parcial de l'element

dc.contributor.author	Carceller-Ferrer, Laura
dc.contributor.author	González del Campo, Aleix
dc.contributor.author	Vila Descals, Carlos
dc.contributor.author	Blay Llinares, Gonzalo
dc.contributor.author	Muñoz, M. Carmen
dc.contributor.author	Pedro, José Ramón
dc.date.accessioned	2022-11-29T13:46:50Z
dc.date.available	2022-11-29T13:46:50Z
dc.date.issued	2022
dc.identifier.citation	Carceller-Ferrer, Laura González del Campo, Aleix Vila Descals, Carlos Blay Llinares, Gonzalo Muñoz, M. Carmen Pedro, José Ramón 2022 Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones Journal of Organic Chemistry 87 7 4538 4549
dc.identifier.uri	https://hdl.handle.net/10550/84620
dc.description.abstract	A diastereo- and enantioselective organocatalytic aldol reaction between alkylidenepyrazolones and trifluoromethyl ketones leading to chiral tertiary alcohols bearing a trifluoromethyl group is presented. The methodology is based on the use of a bifunctional organocatalyst in order to activate the γ-hydrogen atoms of the alkylidenepyrazolone nucleophile and the carbonyl group of the trifluoromethylarylketone providing highly functionalized trifluoromethyl alcohols with moderate yields, excellent diastereoselectivity, and moderate to good enantioselectivity. Experiments monitoring the conversion by 1H NMR and the enantiomeric excess by HPLC with the reaction time showed that full conversion of the starting materials is not achieved and that the enantiomeric excess decreases upon extended times, probably due to the reversibility of the reaction.
dc.language.iso	eng
dc.relation.ispartof	Journal of Organic Chemistry, 2022, vol. 87, num. 7, p. 4538-4549
dc.subject	Catàlisi
dc.subject	Química orgànica
dc.title	Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones
dc.type	journal article	es_ES
dc.date.updated	2022-11-29T13:46:50Z
dc.identifier.doi	10.1021/acs.joc.1c02817
dc.identifier.idgrec	151064
dc.rights.accessRights	open access	es_ES