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Use of Polymer-Supported 4-(N,N-Dimethylamino)pyridine in a Formal Conjugate Addition/Elimination Mediated by an N-Ylide Generated In Situ for the Construction of Highly Functionalized Itaconimides/Alkenes

Saha, Suman K. ; Jain, Anshul ; Kumari, Akanksha ; Bhutia, Tshering Sangmo ; Agrawat, Chanchal ; Rana, Nirmal K.

Synlett, 2023-04, Vol.34 (6), p.667-672 [Periódico revisado por pares]

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Título:
Use of Polymer-Supported 4-(N,N-Dimethylamino)pyridine in a Formal Conjugate Addition/Elimination Mediated by an N-Ylide Generated In Situ for the Construction of Highly Functionalized Itaconimides/Alkenes
Autor: Saha, Suman K. ; Jain, Anshul ; Kumari, Akanksha ; Bhutia, Tshering Sangmo ; Agrawat, Chanchal ; Rana, Nirmal K.
Assuntos: cluster
É parte de: Synlett, 2023-04, Vol.34 (6), p.667-672
Descrição: Abstract A simple, mild, and metal-free cascade reaction has been developed for the construction of highly functionalized olefins. The approach relies on the initial formation of [3+2]-cycloadducts from a pyridinium ylide generated in situ from polymer-bound DMAP (PS-DMAP) with an N -substituted maleimide or an α,β-unsaturated β-keto ester. The cycloadduct decomposes to regenerate supported DMAP and yield a functionalized itaconimide or olefin. The method has a broad substrate scope. The alkene product has been further transformed into trisubstituted furan. PS-DMAP could be reused for five cycles.
Editor: Rüdigerstraße 14, 70469 Stuttgart, Germany: Georg Thieme Verlag KG
Idioma: Inglês

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