RT info:eu-repo/semantics/article
T1 Enantioselective synthesis of 3-hydroxy- and 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of terminal alkynes to isatins and isatin-derived ketimines
A1 Prieto, Elena
A1 Martín, Jorge D.
A1 Nieto Román, Francisco Javier
A1 Andrés Juan, Celia
K1 Catálisis enantioselectiva, compuestos organozíncicos, alquinilación, isatinas e iminas derivadas de isatinas
K1 2306.99 Química Orgánica-Síntesis enatioselectiva
AB A common protocol for enantioselective alkynylation of isatins and isatin-derived ketimines using terminalalkynes and Me2Zn in the presence of a catalytic amount of a chiral perhydro-1,3-benzoxazine with moderate to excellent enantioselectivity under mild reaction conditions is described. The additions to ketimines present a novel approach to chiral amines being derivatives of oxindoles. The reaction is broad in scope with respect to aryl- and alkyl-substituted terminal alkynes and isatin derivatives. In isatins, the alkynylation occurs at the Si face of the carbonyl group, whereas in the ketimine derivatives it occurs at the Re face of the imine.
PB The Royal Society of Chemistry
SN 1477-0520
YR 2023
FD 2023
LK https://uvadoc.uva.es/handle/10324/63063
UL https://uvadoc.uva.es/handle/10324/63063
LA spa
NO Organic and Biomolecular. Chemistry, 2023, vol.21, n 34, p 6940-69-48
NO Producción Científica
DS UVaDOC
RD 22-dic-2024