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Synfacts 2009(9): 1036-1036  
DOI: 10.1055/s-0029-1217790
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Ring Opening of meso-Aziridines with TMS-Protected Thiophenol

Contributor(s): Benjamin List, Steffen Müller
G. Della Sala*, A. Lattanzi
University of Salerno, Fisciano, Italy
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Publikationsdatum:
21. August 2009 (online)

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Significance

The authors report an organocatalytic desymmetrization of meso-aziridines 1 via ring opening with (phenylthio)trimethylsilane (2) to give the corresponding acylaminothioethers 4 in good yields and enantiomeric ratios up to 99.5:0.5. The catalytically active species, a chiral Lewis acid, is formed in situ from the reaction of the chiral phosphoric acid 3 with silylthioether 2.