Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition

A novel approach to synthesize chiral 1,2-oxazinane spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition reaction between methyleneindolinones and γ-aminooxy-α,β-unsaturated ester has been disclosed. Furthermore, a hydrazide 1,4-synthon is designed and synthesized to construct chiral hexah...

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Detalles Bibliográficos
Autores principales: Tian, Heng-Zhi, Tang, Qing-Gang, Lin, Guo-Qiang, Sun, Xing-Wen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9128346/
https://www.ncbi.nlm.nih.gov/pubmed/35685709
http://dx.doi.org/10.1039/d2ra02759c
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author Tian, Heng-Zhi
Tang, Qing-Gang
Lin, Guo-Qiang
Sun, Xing-Wen
author_facet Tian, Heng-Zhi
Tang, Qing-Gang
Lin, Guo-Qiang
Sun, Xing-Wen
author_sort Tian, Heng-Zhi
collection PubMed
description A novel approach to synthesize chiral 1,2-oxazinane spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition reaction between methyleneindolinones and γ-aminooxy-α,β-unsaturated ester has been disclosed. Furthermore, a hydrazide 1,4-synthon is designed and synthesized to construct chiral hexahydropyridazin spirocyclic scaffolds with methyleneindolinones via [4 + 2] cycloaddition reaction. Both reactions give corresponding products in good to excellent yield, excellent diastereoselectivity and good enantioselectivity.
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spelling pubmed-91283462022-06-08 Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition Tian, Heng-Zhi Tang, Qing-Gang Lin, Guo-Qiang Sun, Xing-Wen RSC Adv Chemistry A novel approach to synthesize chiral 1,2-oxazinane spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition reaction between methyleneindolinones and γ-aminooxy-α,β-unsaturated ester has been disclosed. Furthermore, a hydrazide 1,4-synthon is designed and synthesized to construct chiral hexahydropyridazin spirocyclic scaffolds with methyleneindolinones via [4 + 2] cycloaddition reaction. Both reactions give corresponding products in good to excellent yield, excellent diastereoselectivity and good enantioselectivity. The Royal Society of Chemistry 2022-05-24 /pmc/articles/PMC9128346/ /pubmed/35685709 http://dx.doi.org/10.1039/d2ra02759c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Tian, Heng-Zhi
Tang, Qing-Gang
Lin, Guo-Qiang
Sun, Xing-Wen
Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title_full Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title_fullStr Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title_full_unstemmed Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title_short Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
title_sort asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9128346/
https://www.ncbi.nlm.nih.gov/pubmed/35685709
http://dx.doi.org/10.1039/d2ra02759c
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