Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives

CONNON, STEPHEN; MC CABE, THOMAS; WATSON, GRAEME WILLIAM

Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives

Files

Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives.pdf (275.61 KB)

Date

2006

Authors

CONNON, STEPHEN

MC CABE, THOMAS

WATSON, GRAEME WILLIAM

Publisher

Royal Society of Chemistry

Citation

Ciaran O. Dalaigh, Stephen J. Hynes, John E. O'Brien, Thomas McCabe, Declan J. Maher, Graeme W. Watson and Stephen J. Connon, Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives , Organic and Biomolecular Chemistry, 4, 14, 2006, 2785-2793

Abstract

The development of a new class of chiral 4-N,N-dialkylaminopyridine acyl-transfer catalysts capable of exploiting both van der Waals (?) 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)-?,?-diarylprolinol are considerably superior to analogues devoid of a tertiary hydroxyl moiety and possess high activity and selectivity across a broad range of substrates.