Visible-light photoredox catalysis in flow.
Ontology highlight
ABSTRACT:
SUBMITTER: Tucker JW
PROVIDER: S-EPMC3496249 | biostudies-literature | 2012 Apr
REPOSITORIES: biostudies-literature
Publications
Visible-light photoredox catalysis in flow.
Tucker Joseph W JW Zhang Yuan Y Jamison Timothy F TF Stephenson Corey R J CR
Angewandte Chemie (International ed. in English) 20120316 17
Similar Datasets
Project description:(±)-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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