Synthesis and NMR Binding Studies towards Rational Design of a Series of Electron-Withdrawing Diamide Receptors/Organocatalysts
✍ Scribed by Michael Kinsella; Patrick G. Duggan; Jimmy Muldoon; Kevin S. Eccles; Simon E. Lawrence; Claire M. Lennon
- Book ID
- 102174129
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 444 KB
- Volume
- 2011
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
A related series of bisamides have been evaluated for rational correlation between anion complexation and organocatalysis: remarkable enhancement of hydrogen bonding to anions was observed along with significant increases in catalytic activity in the Baylis–Hillman reaction. In addition, X‐ray crystallography showed a large degree of pre‐organisation was observed in one receptor by incorporation of bis(trifluoromethyl)aniline groups along with a thioamide functionality. A novel bifunctional amide/N‐acylsulfonamide within the series gave the best catalytic profile.