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Synthesis of β-Silyl α-Amino Acids via Visible-Light-Mediated Hydrosilylation.

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An expedient synthesis of β-silyl α-amino acids is reported via the application of visible-light-mediated hydrosilylation. The reaction utilizes readily accessible and structurally diverse hydrosilanes to provide radicals for conjugate addition… Click to show full abstract

An expedient synthesis of β-silyl α-amino acids is reported via the application of visible-light-mediated hydrosilylation. The reaction utilizes readily accessible and structurally diverse hydrosilanes to provide radicals for conjugate addition to dehydroalanine ester and analogues. Notably, the use of chiral methyleneoxazolidinone as the substrate and chiral inducer enabled the highly stereoselective synthesis. Furthermore, the reaction could also be performed in a continuous flow fashion and scaled up to the gram scale.

Keywords: amino acids; silyl amino; mediated hydrosilylation; light mediated; visible light; synthesis silyl

Journal Title: Organic letters
Year Published: 2021

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