4.7 Article

Enantioselective Synthesis of Dihydrocoumarins via N-Heterocyclic Carbene-Catalyzed Cycloaddition of Ketenes and o-Quinone Methides

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 17, Pages 2822-2826

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900544

Keywords

asymmetric catalysis; cycloadditions; dihydrocoumarins; ketenes; N-heterocyclic carbenes

Funding

  1. National Natural Science Foundation of China [20602036, 20872143]
  2. Ministry of Science and Technology of China [2009ZX09501-018]
  3. Chinese Academy of Sciences

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Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [4+2] cycloaddition reaction of alky(aryl)ketenes and o-quinone methides to give the corresponding 3,3,4-trisubstituted 3,4-dihydrocoumarins in good yields with good diastereoselectivities and excellent enantioselectivities.

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