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Synfacts 2010(7): 0825-0825  
DOI: 10.1055/s-0029-1220116
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Kinetic Resolution of Thiols

Contributor(s): Benjamin List, Saihu Liao
A. Peschiulli, B. Procuranti, C. J. O’Connor, S. J. Connon*
The University of Dublin, Ireland
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

An efficient direct acylative kinetic resolution of racemic secondary thiols 1 was reported by the authors, using a novel sulfonamide catalyst derived from a cinchona alkaloid. Under optimal conditions (10 mol% catalyst loading, ;-30 ˚C in MTBE), with 2 as the electrophile, various secondary aromatic thiols can be resolved with high er at ˜50% conversion. The selectivity (S = k fast/k slow) of the resolution is in the range of 50-275. In addition, during the kinetic resolution of the thiols, a simultaneous desymmetrization of a meso-anhydride electrophile (like 2) also occurred with excellent enantioselectivity.