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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
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.