Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

Michael Kinsella; Patrick Duggan; Jimmy Muldoon; Kevin S. Eccles; Simon E. Lawrence; Claire Lennon

doi:10.1002/ejoc.201001439

Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

Michael Kinsella, Patrick Duggan, Jimmy Muldoon, Kevin S. Eccles, Simon E. Lawrence, Claire Lennon

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1125-1132
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	6
DOIs	https://doi.org/10.1002/ejoc.201001439
Publication status	Published - Feb 2011

Keywords

Amides
Anion binding
Anions
H-bonding
Organocatalysis

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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.",

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AU - Kinsella, Michael

AU - Duggan, Patrick

AU - Muldoon, Jimmy

AU - Eccles, Kevin S.

AU - Lawrence, Simon E.

AU - Lennon, Claire

PY - 2011/2

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AB - 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.

KW - Amides

KW - Anion binding

KW - Anions

KW - H-bonding

KW - Organocatalysis

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EP - 1132

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 6

ER -

Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

Abstract

Keywords

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