4.8 Article

Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of Alkylidenecyclopropanes

Journal

ORGANIC LETTERS
Volume 19, Issue 23, Pages 6288-6291

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02989

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Funding

  1. NSFC [21632003, 21372105, 21572087]
  2. 111 program from the MOE of P. R. China
  3. Syngenta Company

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A novel visible-light-induced aza-pinacol rearrangement was developed for the first time. In this approach, the addition of the N-centered radical to the C=C bond of alkylidenecydopropanes delivers a variety of cyclobutanimines and gamma-butyrolactones, with all-carbon quaternary centers via the ring expansion of the cyclopropyl group, in moderate to good yields under mild reaction conditions.

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