Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers
Organic & Biomolecular ChemistryPublished 1 January 2013Open access
Fangle Hu, Yin Wei, Min Shi, Suresh Pindi, Guigen Li
Citations97
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TL;DR
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, resulting in biomedically important 3-substituted 3-amino-2-oxindoles in good yields and with excellent enantioselectivity.
Abstract
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.
Keywords
Chemistry
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