2026-05-05T10:25:23Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/630632024-05-15T19:00:59Zcom_10324_28542com_10324_952com_10324_894com_10324_1187com_10324_931col_10324_28543col_10324_1408

Prieto, Elena Martín, Jorge D. Nieto Román, Francisco Javier Andrés Juan, Celia 2023-11-17T10:38:02Z 2023-11-17T10:38:02Z 2023 Organic and Biomolecular. Chemistry, 2023, vol.21, n 34, p 6940-69-48 1477-0520 https://uvadoc.uva.es/handle/10324/63063 10.1039/d3ob01023f 6940 34 6948 Organic & Biomolecular Chemistry 21 1477-0539 A common protocol for enantioselective alkynylation of isatins and isatin-derived ketimines using terminal alkynes 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. spa info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc/3.0/ The Royal Society of Chemistry Attribution-NonCommercial 3.0 Unported Licence 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 info:eu-repo/semantics/article