ArticleThe Journal of organic chemistry2015
Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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The trial behind it
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Who cites it
4 citing papers in PubMed.
- Stereoselective Synthesis of Benzo[ACS omega · 2022Article
- Photoredox-Catalyzed C-H Functionalization Reactions.Chemical reviews · 2022Review
- Synthesis of Tetrabenazine and Its Derivatives, Pursuing Efficiency and Selectivity.Molecules (Basel, Switzerland) · 2020Review
- Redox-Annulation of Cyclic Amines and β-Ketoaldehydes.Organic letters · 2016Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.
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Registered trials
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