RT Journal Article
T1 Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles
A1 Castroagudín Campos, Mariña
A1 Lobato, Rubén
A1 Martínez García, Lucas
A1 Sardina López, Francisco Javier
A1 Paleo Pillado, María Rita
K1 Alcohols
K1 Anions
K1 Electrophiles
K1 Organic compounds
AB Bis-enolates with extended π-conjugation, prepared by alkali metal-mediated reduction of several aromatic and unsaturated diesters, can be efficiently and regioselectively alkylated with very hindered C-electrophiles, such as neopentyl, secondary and tertiary alkyl halides, and tosylates. A one-step synthesis of 4-alkyl phthalates was derived from the reductive alkylation of a phthalate diester with hindered halides followed by rearomatization with oxygen. Additionally, synthetic protocols have been developed to efficiently prepare complex fused- or spiro-bicycles from diisopropyl phthalate in just one or two steps
PB The American Chemical Society
SN 1361-1378
YR 2019
FD 2019
LK http://hdl.handle.net/10347/32383
UL http://hdl.handle.net/10347/32383
LA eng
NO Castroagudín, M.,Lobato, R., Martínez García, L., Sardina, F.J., Paleo, M.R. (2019). Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles. "The journal of organic chemistry", vol.84, 15805-15816
NO This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2019 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b01961
NO Financial support from Ministerio de Economía y Competitividad of Spain (CTQ2017-84354-P), Xunta de Galicia (GRC 2014/029 and Centro singular de investigación de Galicia accreditation 2016-2019, ED431G/09), and the European Union (European Regional Development Fund-ERDF) is gratefully acknowledged.
DS Minerva
RD 24 abr 2026