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Issue 14, 2006
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Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives

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Abstract

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

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

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Supplementary files

Article information


Submitted
30 Mar 2006
Accepted
02 Jun 2006
First published
20 Jun 2006

Org. Biomol. Chem., 2006,4, 2785-2793
Article type
Paper

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

C. Ó. Dálaigh, S. J. Hynes, J. E. O'Brien, T. McCabe, D. J. Maher, G. W. Watson and S. J. Connon, Org. Biomol. Chem., 2006, 4, 2785
DOI: 10.1039/B604632K

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