title: Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives.
abstract: The development of a new class of chiral 4-N,N-dialkylaminopyridine acyl-transfer catalysts capable of exploiting both van der Waals (pi) and H-bonding interactions to allow remote chiral information to stereochemically control the kinetic resolution of sec-alcohols with moderate to excellent selectivity (s = 6-30). Catalysts derived from (S)-alpha,alpha-diarylprolinol are considerably superior to analogues devoid of a tertiary hydroxyl moiety and possess high activity and selectivity across a broad range of substrates.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
authors.forename: Ciarán O
authors.initials: CO
authors.lastname: Dálaigh
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Hynes
authors.forename: John E
authors.initials: JE
authors.lastname: O'Brien
authors.forename: Thomas
authors.initials: T
authors.lastname: McCabe
authors.forename: Declan J
authors.initials: DJ
authors.lastname: Maher
authors.forename: Graeme W
authors.initials: GW
authors.lastname: Watson
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Connon
mesh_terms: D000215:Acylation; D002384:Catalysis; D007477:Ions; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007477:Ions; D011725:Pyridines; D011726:Pyridinium Compounds