Synthesis and NMR Binding Studies towards Rational Design of a Series of Electron‐Withdrawing Diamide Receptors/Organocatalysts | Zendy

Kinsella Michael | Zendy; Duggan Patrick G. | Zendy; Muldoon Jimmy | Zendy; Eccles Kevin S. | Zendy; Lawrence Simon E. | Zendy; Len Claire M. | Zendy

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Synthesis and NMR Binding Studies towards Rational Design of a Series of Electron‐Withdrawing Diamide Receptors/Organocatalysts

Author(s) -

Kinsella Michael,

Duggan Patrick G.,

Muldoon Jimmy,

Eccles Kevin S.,

Lawrence Simon E.,

Len Claire M.

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201001439

Subject(s) - chemistry , thioamide , bifunctional , trifluoromethyl , rational design , catalysis , amide , organocatalysis , hydrogen bond , aniline , stereochemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , organic chemistry , molecule , nanotechnology , alkyl , materials science

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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