4.7 Article

Striking Difference between Succinimidomethyl and Phthalimidomethyl Radicals in Conjugate Addition to Alkylidenemalonate Initiated by Dimethylzinc

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 9, Pages 3809-3817

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00485

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Funding

  1. Japan Society for the Promotion of Science
  2. Japanese Ministry of Education, Culture, Sports, Science and Technology

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We used dimethylzinc to develop a conjugate addition reaction of imidomethyl radicals to alkylidenemalonates, in which we observed a significant difference between succinimidomethyl and phthalimidomethyl radicals. This reaction provides new access to gamma-aminobutyric acid derivatives, which often function as neurotransmitters.

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