Copper-Mediated Divergent Reactivity of Allene-Tethered Carbamates under Radical Conditions

By judicious selection of reaction conditions, the controllable copper-promoted bromoheterocyclization or the sulfonylation/dimerization of allenyl carbamates to access 5-bromo-6-methylene-1,3-oxazinan-2-ones or bis(γ-amino vinyl sulfones) has been implemented. The described method, which is easy to...

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Bibliographic Details
Authors: Toledano-Pinedo, Mireia, Quirós, M Teresa, Padrón, Ignacio, Halka, Dawid, Georgiou, Xenios, Martínez Del Campo, Teresa, Luna, Amparo, Almendros, Pedro
Format: article
Status:Published version
Publication Date:2025
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/393159
Online Access:http://hdl.handle.net/10261/393159
https://api.elsevier.com/content/abstract/scopus_id/105008037127
Access Level:Open access
Description
Summary:By judicious selection of reaction conditions, the controllable copper-promoted bromoheterocyclization or the sulfonylation/dimerization of allenyl carbamates to access 5-bromo-6-methylene-1,3-oxazinan-2-ones or bis(γ-amino vinyl sulfones) has been implemented. The described method, which is easy to scale up and exhibits good functional group tolerance, displays exquisite selectivity control for the preparation of two structurally different compounds starting from the same precursors under free radical conditions.