De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition

Conboy, Aífe; Goodfellow, Alister S.; Kasten, Kevin; Dunne, Joanne; Cordes, David B.; Bühl, Michael; Smith, Andrew D.

doi:10.1039/d4sc01410c

Chem. Sci.

2024

DOI: 10.1039/d4sc01410c

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De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition

Aífe Conboy,

Alister S. Goodfellow,

Kevin Kasten

et al.

Abstract: Moderate diastereoselectivity (typically 70:30 dr) is observed in the isothiourea-catalysed [2+2]-cycloaddition of C(1)-ammonium enolates with pyrazol-4,5-diones to generate spirocyclic β lactones, but subsequent ring-opening with morpholine generatesβ hydroxyamide products with...

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2024

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Cited by 2 publications

References 87 publications

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Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine

Yang,

Wang

2024

Molecular Catalysis

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Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine

Yang,

Wang

2024

Molecular Catalysis

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One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening

Nimmo,

Kasten,

White

et al. 2024

Molecules

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Malamides (diamide derivatives of malic acid) are prevalent in nature and of significant biological interest, yet only limited synthetic methods to access functionalised enantiopure derivatives have been established to date. Herein, an effective synthetic method to generate this molecular class is developed through in situ formation of spirocyclic β-lactone-oxindoles (employing a known enantioselective isothiourea-catalysed formal [2+2] cycloaddition of C(1)-ammonium enolates and isatin derivatives) followed by a subsequent dual ring-opening protocol (of the β-lactone and oxindole) with amine nucleophiles. The application of this protocol is demonstrated across twelve examples to give densely functionalised malamide derivatives with high enantio- and diastereo-selectivity (up to >95:5 dr and >99:1 er).

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De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition

Abstract: Moderate diastereoselectivity (typically 70:30 dr) is observed in the isothiourea-catalysed [2+2]-cycloaddition of C(1)-ammonium enolates with pyrazol-4,5-diones to generate spirocyclic β lactones, but subsequent ring-opening with morpholine generatesβ hydroxyamide products with...

Cited by 2 publications

References 87 publications

Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine

Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine

One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening

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