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Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

ABSTRACT: Harnessing the chemistry of onium ylide intermediates generated from transition metal catalysis is a powerful strategy to convert simple precursors into complex scaffolds. While the chemistry of onium ylides has been studied for over three decades, transformations of aziridinium ylides have just recently emerged as a versatile way to exploit the strain of these reactive intermediates to furnish densely functionalized N-heterocycles in a highly stereocontrolled manner. Herein, we provide a short overview of the key concepts and recent developments in this area, with a focus on how mechanistic studies to delineate the factors controlling the reactivity of aziridinium ylides can stimulate fruitful future investigations.

SUBMITTER: Dequina HJ

PROVIDER: S-EPMC7929518 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Dequina Hillary J HJ Schomaker Jennifer M JM

Trends in chemistry 20200902 10

Harnessing the chemistry of onium ylide intermediates generated from transition metal catalysis is a powerful strategy to convert simple precursors into complex scaffolds. While the chemistry of onium ylides has been studied for over three decades, transformations of aziridinium ylides have just recently emerged as a versatile way to exploit the strain of these reactive intermediates to furnish densely functionalized <i>N</i>-heterocycles in a highly stereocontrolled manner. Herein, we provide a ...[more]

PMID: 33665590

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