A reusable polymer anchored pyridine mediated formal [4 + 1] annulation reaction for the diastereoselective synthesis of 2,3-dihydrobenzofurans

Akanksha Kumari; Anshul Jain; Khyati Shukla; Ranjan Patra; Nirmal K. Rana

doi:10.1039/D3OB00804E

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A reusable polymer anchored pyridine mediated formal [4 + 1] annulation reaction for the diastereoselective synthesis of 2,3-dihydrobenzofurans†

Akanksha Kumari,

^a Anshul Jain,

^a Khyati Shukla,^b Ranjan Patra

^c and Nirmal K. Rana

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Indian Institute of Technology Jodhpur, Rajasthan 342030, India
E-mail: nirmalrana@iitj.ac.in

^b Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, UP, India

^c Amity Institute of Click Chemistry Research & Studies, Amity University, Uttar Pradesh 201303, India

Abstract

We have developed a highly stereoselective formal [4 + 1] annulation reaction to construct trans-2,3-dihydrobenzofurans utilising in situ generated supported pyridinium ylide. This approach has excellent substrate versatility and gram-scale synthesis capability. Moreover, the polymer-anchored pyridine has been recovered and reused multiple times. The product has been transformed into valuable molecules.

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DOI: https://doi.org/10.1039/D3OB00804E
Article type: Communication
Submitted: 22 May 2023
Accepted: 19 Jun 2023
First published: 21 Jun 2023

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Org. Biomol. Chem., 2023,21, 5542-5546

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A reusable polymer anchored pyridine mediated formal [4 + 1] annulation reaction for the diastereoselective synthesis of 2,3-dihydrobenzofurans

A. Kumari, A. Jain, K. Shukla, R. Patra and N. K. Rana, Org. Biomol. Chem., 2023, 21, 5542 DOI: 10.1039/D3OB00804E

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Organic & Biomolecular Chemistry

A reusable polymer anchored pyridine mediated formal [4 + 1] annulation reaction for the diastereoselective synthesis of 2,3-dihydrobenzofurans†

Abstract

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A reusable polymer anchored pyridine mediated formal [4 + 1] annulation reaction for the diastereoselective synthesis of 2,3-dihydrobenzofurans

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