Issue 39, 2023

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Abstract

An important objective in organic synthesis and medicinal chemistry is the capacity to access structurally varied and complex molecules rapidly and affordably from easily available starting materials. Herein, a protocol for the structurally divergent synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans has been developed via chiral bifunctional urea catalyzed reaction between aurone-derived α,β-unsaturated imine and ynone followed by switchable divergent annulation reactions by Lewis base catalysts (DBU and PPh3) with concomitant epimerization. The skeletally diversified products were formed in high yields with high diastereo- and enantioselectivities. Computational analysis with DFT and accurate DLPNO-CCSD(T) has been employed to gain deeper insights into mechanistic intricacies and investigate the role of chiral and Lewis base catalysts in skeletal diversity.

Graphical abstract: Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Associated articles

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Article information

Article type
Edge Article
Submitted
26 jún 2023
Accepted
04 sep 2023
First published
07 sep 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 10768-10776

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

R. Khuntia, S. K. Mahapatra, L. Roy and S. Chandra Pan, Chem. Sci., 2023, 14, 10768 DOI: 10.1039/D3SC03239F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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