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

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

School of Chemistry

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

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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10.1002/ejoc.201001439

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

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.",

keywords = "Amides, Anion binding, Anions, H-bonding, Organocatalysis",

author = "Michael Kinsella and Duggan, \{Patrick G.\} and Jimmy Muldoon and Eccles, \{Kevin S.\} and Lawrence, \{Simon E.\} and Lennon, \{Claire M.\}",

year = "2011",

month = feb,

doi = "10.1002/ejoc.201001439",

language = "English",

pages = "1125--1132",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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T1 - Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

AU - Kinsella, Michael

AU - Duggan, Patrick G.

AU - Muldoon, Jimmy

AU - Eccles, Kevin S.

AU - Lawrence, Simon E.

AU - Lennon, Claire M.

PY - 2011/2

Y1 - 2011/2

N2 - 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.

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

UR - https://www.scopus.com/pages/publications/79851505107

U2 - 10.1002/ejoc.201001439

DO - 10.1002/ejoc.201001439

M3 - Article

AN - SCOPUS:79851505107

SN - 1434-193X

SP - 1125

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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