Synlett 2023; 34(06): 667-672
DOI: 10.1055/a-1934-1189
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Chemical Synthesis and Catalysis in India

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

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

This work was financially supported by the Science and Engineering Research Board (SERB), India, (CRG/2020/001940) and the Council of Scientific and Industrial Research (CSIR), India, (02(0424)/21/EMR-II).


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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.

Supporting Information



Publication History

Received: 30 May 2022

Accepted after revision: 30 August 2022

Accepted Manuscript online:
30 August 2022

Article published online:
28 September 2022

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