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Bis-enolates with Extended π‑Conjugation Are Powerful Nucleophiles: A Study of Their Alkylation Reactions with Very Hindered C‑Electrophiles

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journal contribution
posted on 11.12.2019, 23:14 by Mariña Castroagudín, Rubén Lobato, Lucas Martínez-García, F. Javier Sardina, M. Rita Paleo
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.