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A Strategy toward Cyclic Topologies Based on the Dynamic Behavior of a Bis(hindered amino)disulfide Linker.
Tsurumi, Nao; Takashima, Rikito; Aoki, Daisuke; Kuwata, Shigeki; Otsuka, Hideyuki.
Afiliación
  • Tsurumi N; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Takashima R; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Aoki D; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Kuwata S; JST PRESTO Researcher, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.
  • Otsuka H; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8550, Japan.
Angew Chem Int Ed Engl ; 59(11): 4269-4273, 2020 Mar 09.
Article en En | MEDLINE | ID: mdl-31919955
A simple and efficient method to generate macrocyclic structures has been developed based on the dynamic behavior of the linker bis(2,2,6,6-tetramethylpiperidin-1-yl)disulfide (BiTEMPS). The prime linear structure was transformed into a (macro)cycle using the following sequence: 1) thiol-ene reaction with a BiTEMPS derivative to afford the linear precursor, then 2) an entropy-driven transformation induced by diluting and heating. The radicals generated from BiTEMPS upon heating are highly tolerant toward a variety of chemical species, including oxygen and olefins, but they exhibit high reactivity in exchange reactions, which can be applied to the topology transformation of various skeletons. The advantages of the present method, namely, its procedural simplicity and substrate versatility, are demonstrated by the gram-scale synthesis of cyclic compounds with low and relatively high molecular weight.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2020 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2020 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Alemania