4.8 Article

Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive Elimination from Rhodacyclopentanones

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 36, Pages 11465-11468

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07046

Keywords

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Funding

  1. European Research Council via EU (ERC) [639594]
  2. Bristol Chemical Synthesis Centre for Doctoral Training (EPSRC) [EP/G036764/1]
  3. Royal Society
  4. European Research Council (ERC) [639594] Funding Source: European Research Council (ERC)
  5. EPSRC [EP/L011999/1, EP/K03927X/1] Funding Source: UKRI
  6. Engineering and Physical Sciences Research Council [EP/L011999/1, 1114267, EP/K03927X/1] Funding Source: researchfish

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Rhodacydopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be captured by pendant nucleophiles prior to collapse to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively.

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