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Reactivity of lithium β‑ketocarboxylates: the role of lithium salts

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Reactivity of lithium β‑ketocarboxylates: the role of lithium salts

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dc.contributor.author	Berton, Mateo Otao
dc.contributor.author	Mello, Rossella C. C.
dc.contributor.author	Williard, Paul G.
dc.contributor.author	González Núñez, María Elena
dc.date.accessioned	2018-07-04T13:06:01Z
dc.date.available	2018-11-08T05:45:05Z
dc.date.issued	2017
dc.identifier.citation	Berton, Mateo Otao Mello, Rossella C. C. Williard, Paul G. González Núñez, María Elena 2017 Reactivity of lithium β‑ketocarboxylates: the role of lithium salts Journal of the American Chemical Society 139 48 17414 17420
dc.identifier.uri	http://hdl.handle.net/10550/66909
dc.description.abstract	Lithium beta-ketocarboxylates 1(COOLi), prepared by the reaction of lithium enolates 2(Li+) with carbon dioxide, readily decarboxylate in THF solution unless in the presence of lithium salts, in which case they are indefinitely stable at room temperature in inert atmosphere. The availability of stable THF solutions of lithium beta-ketocarboxylates 1(COOLi) in the absence of carbon dioxide allowed reactions to take place with nitrogen bases and alkyl halides 3 to give alpha-alkyl ketones 1(R) after acidic hydrolysis. The sequence thus represents the use of carbon dioxide as a removable directing group for the selective monoalkylation of lithium enolates 2(Li+). The roles of lithium salts in preventing the decarboxylation and disproportionation reactions of lithium beta-ketocarboxylates 1(COOLi), and in determining the course of the reaction with bases and alkyl halides 3, are discussed.
dc.language.iso	eng
dc.relation.ispartof	Journal of the American Chemical Society, 2017, vol. 139, num. 48, p. 17414-17420
dc.subject	Química orgànica
dc.title	Reactivity of lithium β‑ketocarboxylates: the role of lithium salts
dc.type	journal article	es_ES
dc.date.updated	2018-07-04T13:06:02Z
dc.identifier.doi	10.1021/jacs.7b08450
dc.identifier.idgrec	121487
dc.embargo.terms	1 year
dc.rights.accessRights	open access	es_ES