4.6 Article

Formal [3+3] annulation of isatin-derived 2-bromoenals with 1,3-dicarbonyl compounds enabled by Lewis acid/N-heterocyclic carbene cooperative catalysis

Journal

RSC ADVANCES
Volume 6, Issue 22, Pages 18601-18606

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra27848a

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Funding

  1. National Natural Science Foundation of China [21572270, 81172933]
  2. Jiangsu Provincial Natural Science Foundation of China [BK20131305]
  3. College Students Innovation Project for the R&D of Novel Drugs [J1030830]
  4. National Undergraduate Training Program for Innovation and Entrepreneurship
  5. Priority Academic Program Development of Jiangsu Higher Education Institutions

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A series of novel isatin-derived 2-bromoenals were synthesized and applied in a formal [3 + 3] annulation with 1,3-dicarbonyl compounds enabled by a NHC/Lewis acid cooperative catalysis strategy. This newly developed methodology offers rapid access to functionalized spirooxindole d-lactones. The newly synthesized isatin-derived 2-bromoenals may be further used as potential electrophilic 1,3-synthons for the diversity-oriented synthesis of spirooxindoles.

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