Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives.
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.
Dálaigh
Ciarán O
CO
Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
Hynes
Stephen J
SJ
O'Brien
John E
JE
McCabe
Thomas
T
Maher
Declan J
DJ
Watson
Graeme W
GW
Connon
Stephen J
SJ
D000215:Acylation; D002384:Catalysis; D007477:Ions; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D007477:Ions; D011725:Pyridines; D011726:Pyridinium Compounds