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Synfacts 2005(3): 0315-0315  
DOI: 10.1055/s-2005-921642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

4-(Dimethylamino)pyridine Analogue Bearing a Sulfoxide as Chiral Inducer

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Poisson, M. Penhoat, C. Papamicaël, G. Dupas, V. Dalla, F. Marsais, V. Levacher*
Université et INSA de Rouen, France
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The authors describe a one-step synthesis of a DMAP-analogue bearing a sulfoxide group that effects the kinetic resolution of secondary alcohols. Various racemic aryl-substituted secondary alcohols were tested by acylation with 5 mol% of the catalyst and showed s-factors ranging from 1.3-4.5 depending on substrate, acylating reagent, temperature and solvent.