Organocatalytic asymmetric synthesis of oxazolidino spiropyrazolinones via N , O -acetalization/aza Michael addition domino reaction between N -Boc pyrazolinone ketimines and γ-hydroxyenones

Organocatalytic asymmetric synthesis of oxazolidino spiropyrazolinones via N , O -acetalization/aza Michael addition domino reaction between N -Boc pyrazolinone ketimines and γ-hydroxyenones

A squaramide-catalyzed asymmetric , -acetalization/aza Michael addition domino reaction between -Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. A hydroquinine derived bifunctional squaramide catalyst...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-03, Vol.21 (11), p.2361-2369
Hauptverfasser: Gil-Ordóñez, Marta, Martín, Laura, Maestro, Alicia, Andrés, José M
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Sprache:eng
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Asymmetric synthesis
Asymmetry
Cascade chemical reactions
Catalysts
Imines
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container_issue 11
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container_title Organic & biomolecular chemistry
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creator Gil-Ordóñez, Marta
Martín, Laura
Maestro, Alicia
Andrés, José M
description A squaramide-catalyzed asymmetric , -acetalization/aza Michael addition domino reaction between -Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. A hydroquinine derived bifunctional squaramide catalyst was found to be the most effective for this cascade spiroannulation. This new protocol allows the generation of two stereocenters and the desired products are obtained in good yields with moderate to good diastereoselectivities (up to 3.3 : 1 dr) and high enantioselectivities (up to >99% ee) from a range of substituted -Boc pyrazolinone ketimines and γ-hydroxyenones. The developed protocol is amenable for a scale-up reaction.
doi_str_mv 10.1039/d2ob02290g
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Asymmetric synthesis
Asymmetry
Cascade chemical reactions
Catalysts
Imines
title Organocatalytic asymmetric synthesis of oxazolidino spiropyrazolinones via N , O -acetalization/aza Michael addition domino reaction between N -Boc pyrazolinone ketimines and γ-hydroxyenones
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