4.7 Article

N-Heterocyclic Carbene Catalyzed [3+2] Cycloaddition of Enals with β,γ-Unsaturated α -Ketimino Esters for the Synthesis of Multisubstituted Cyclopentanone

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 4, Pages 807-811

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901144

Keywords

N-heterocyclic carbene; beta,gamma-unsaturated alpha-ketimino esters; cyclopentanone

Funding

  1. National Natural Science Foundation of China [21402037]
  2. Natural Science Foundation of Hebei Province [B2015201175, B2019201081, B2019201101]
  3. Foundation of Hebei Education Department [QN2014106]
  4. Project of Introduction of Overseas Personnel in Hebei Province [C20190503]
  5. Advanced Talents Incubation Program of the Hebei University [801260201299]

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A convenient strategy of N-heterocyclic carbene catalyzed [3+2] cycloaddition of enals with beta,gamma-unsaturated alpha-ketimino esters is developed. This effective protocol features mild reaction conditions and broad substrate scope, which enables the rapid assembly of various benzoxazinone derived cyclopentanone scaffolds in good to high yields with excellent diastereoselectivities.

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