Castroagudín Campos, MariñaLobato, RubénMartínez García, LucasSardina López, Francisco JavierPaleo Pillado, María Rita2024-02-062024-02-062019Castroagudín, 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, 15805-158161361-1378http://hdl.handle.net/10347/32383This 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.9b01961Bis-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 stepsengCopyright © 2019 American Chemical Societyhttp://creativecommons.org/licenses/by-nc-nd/4.0/AlcoholsAnionsElectrophilesOrganic compounds2306 Química orgánica2415 Biología molecularjournal article10.1021/acs.joc.9b019611520-6904open access