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

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...

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Detalles Bibliográficos
Autores principales: Khuntia, Rupkumar, Mahapatra, Sanat Kumar, Roy, Lisa, Chandra Pan, Subhas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10566461/
https://www.ncbi.nlm.nih.gov/pubmed/37829006
http://dx.doi.org/10.1039/d3sc03239f
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author Khuntia, Rupkumar
Mahapatra, Sanat Kumar
Roy, Lisa
Chandra Pan, Subhas
author_facet Khuntia, Rupkumar
Mahapatra, Sanat Kumar
Roy, Lisa
Chandra Pan, Subhas
author_sort Khuntia, Rupkumar
collection PubMed
description 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 PPh(3)) 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.
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spelling pubmed-105664612023-10-12 Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis Khuntia, Rupkumar Mahapatra, Sanat Kumar Roy, Lisa Chandra Pan, Subhas Chem Sci Chemistry 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 PPh(3)) 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. The Royal Society of Chemistry 2023-09-07 /pmc/articles/PMC10566461/ /pubmed/37829006 http://dx.doi.org/10.1039/d3sc03239f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Khuntia, Rupkumar
Mahapatra, Sanat Kumar
Roy, Lisa
Chandra Pan, Subhas
Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title_full Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title_fullStr Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title_full_unstemmed Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title_short Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
title_sort structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10566461/
https://www.ncbi.nlm.nih.gov/pubmed/37829006
http://dx.doi.org/10.1039/d3sc03239f
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