Parallel kinetic resolution of aziridines <i>via</i> chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

Liu, Juan; Du, Yi-Ying; He, Yu-Shi; Liang, Yan; Liu, Shang-Zhong; Li, Yi-Yi; Cao, Yi-Ming

doi:10.1039/d3sc03899h

Chem. Sci.

2023

DOI: 10.1039/d3sc03899h

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Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

Juan Liu,

Yi-Ying Du,

Yu-Shi He

et al.

Abstract: We report a chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of...

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2024

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Cited by 7 publications

References 111 publications

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Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Liu,

Teng,

Zhang

et al. 2024

Angewandte Chemie

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An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single chiral N‐heterocyclic carbene (NHC) catalyst to react with the different enantiomers of the racemic imine substrate in a parallel fashion. Two products bearing distinct structures and opposite stereoselectivities are respectively afforded from the same reaction system in good to excellent yields, enantio‐ and diastereoselectivities. Control experiments and kinetic studies are carried out to probe the kinetic and dynamic properties during the reaction progress. The planar chiral pyridine and lactam products show interesting applications in both asymmetric synthesis and pesticide development.

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Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Liu,

Teng,

Zhang

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Liu,

Teng,

Zhang

et al. 2024

Angew Chem Int Ed

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Synthetic Approaches for the Construction of Chiral Aziridines

Liu,

Han

et al. 2024

Eur J Org Chem

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Optically active aziridines represent a pivotal class of rigid three‐membered nitrogen‐heterocyclic compounds found in natural products, pharmaceuticals, agrochemicals, and functional motifs, which have demonstrated outstanding practicability as therapeutic molecular frameworks, versatile synthetic endpoints, and functional materials in both academic and industrial communities. Recent years have witnessed a broad spectrum of prominent breakthroughs in the field of chiral aziridines due to the aziridine‐based rigid and three‐dimensional pharmacophores, which have resulted in streamlining the drug discovery process. Over the past few decades, particular attention has been directed towards the strategically efficient, versatile, and practical assembly of optically active aziridines. These synthesis approaches have demonstrated great potential in the context of the construction of pharmaceutical molecules, biologically and pharmacologically relevant natural products, and functional materials. In this review, several synthetic strategies for the assembly of chiral aziridines are summarized, which could be divided into five categories; (1) Introduction; (2) Construction of optically active aziridines via reactions of olefines with nitrene sources; (3) Construction of optically active aziridines via reactions of imines with carbenes; (4) Construction of optically active aziridines via reaction of azirines; (5) Construction of optically active aziridines via intramolecular cyclization of amine derivatives.

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Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

Abstract: We report a chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of...

Cited by 7 publications

References 111 publications

Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates

Synthetic Approaches for the Construction of Chiral Aziridines

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