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Asymmetric Organocatalytic Synthesis of aza-Spirocyclic Compounds from Isothiocyanates and Isocyanides

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Asymmetric Organocatalytic Synthesis of aza-Spirocyclic Compounds from Isothiocyanates and Isocyanides

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dc.contributor.author	Laviós, Adrián
dc.contributor.author	Sanz Marco, Amparo
dc.contributor.author	Vila Descals, Carlos
dc.contributor.author	Blay Llinares, Gonzalo
dc.contributor.author	Pedro, José Ramón
dc.date.accessioned	2022-04-05T13:24:47Z
dc.date.available	2022-04-05T13:24:47Z
dc.date.issued	2021
dc.identifier.citation	Laviós, Adrián Sanz Marco, Amparo Vila Descals, Carlos Blay Llinares, Gonzalo Pedro, José Ramón 2021 Asymmetric Organocatalytic Synthesis of aza-Spirocyclic Compounds from Isothiocyanates and Isocyanides European Journal of Organic Chemistry 2021 16 2268 2284
dc.identifier.uri	https://hdl.handle.net/10550/82177
dc.description.abstract	The spirocyclic motif is present in natural products, chiral ligands, and compounds of pharmacological interest. Isothiocyanates as well as isocyanides bearing electron-withdrawing groups in the α-position can be deprotonated and react as formal dipoles on account of the presence of a nucleophilic carbanion and an electrophilic atom in the isothiocyanate or isocyanide functional groups. In the last years a number of procedures involving the formal [3+2] cycloaddition reaction of isothiocyanates or isocyanides with cyclic compounds bearing electrophilic exocyclic double bonds have been developed for the enantioselective synthesis of aza-spirocyclic compounds. Among them, organocatalysis has played a predominant role in the development of asymmetric versions for these reactions. The synthesis of spirooxindoles by using this methodology has received especial attention, although other spirocyclic scaffolds are available depending on the structure of the dipolarophiles and the formal isothiocyanate and isocyanide dipoles.
dc.language.iso	eng
dc.relation.ispartof	European Journal of Organic Chemistry, 2021, vol. 2021, num. 16, p. 2268-2284
dc.subject	Química orgànica
dc.subject	Compostos orgànics
dc.title	Asymmetric Organocatalytic Synthesis of aza-Spirocyclic Compounds from Isothiocyanates and Isocyanides
dc.type	journal article	es_ES
dc.date.updated	2022-04-05T13:24:48Z
dc.identifier.doi	10.1002/ejoc.202100232
dc.identifier.idgrec	146540
dc.rights.accessRights	open access	es_ES