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January 1, 2006Organic & Biomolecular Chemistry56 citationsOpen Access

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

CDCiarán Ó DálaighSHStephen J. HynesJOJohn E. O’Brien

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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 (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.

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Dálaigh et al. (2006) studied this question.

synapsesocial.com/papers/6a4ce4e4133ce5a1f65aa5e1https://doi.org/10.1039/b604632k
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