4.6 Article

Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 12, Pages 1921-1924

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob27495k

Keywords

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Funding

  1. Shanghai Municipal Committee of Science and Technology [11JC1402600]
  2. NIH [R21DA031860-01]
  3. Robert Welch Foundation [D-1361]
  4. National Basic Research Program of China [(973)-2010CB833302]
  5. Fundamental Research Funds for the Central Universities
  6. National Natural Science Foundation of China [21072206, 20472096, 20872162, 20672127, 21121062, 21102166, 20732008]
  7. NATIONAL INSTITUTE ON DRUG ABUSE [R21DA031860] Funding Source: NIH RePORTER

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The asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and with excellent enantioselectivity (90-99% ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems.

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