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Synlett 1990; 1990(5): 287-289
DOI: 10.1055/s-1990-21068
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Asymmetric Reactions of Sulfoxides Derived from Diastereoselective Oxidation of 2-Alkylthio-2′-hydroxy-1,1′-binaphthalenes

Ottorino De Lucchi* , Davide Fabri
  • *Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy
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Publication Date:
08 March 2002 (online)

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2-Mercapto-2′-hydroxy-1,1′-binaphthalene is the hydroxythiol precursor of a number of sulfides which are oxidized highly diastereoselectively to the respective sulfoxides. The latter undergo the rich chemistry of sulfinyl compounds, as represented by the generation of the anion at the α carbon with butyllithium and the reduction of the benzoyl derivative. Overall, the present reaction sequence constitutes a potentially recyclable method for the diastereoselective preparation of sulfoxides, which allows the formation of new chiral centers via synergistic contribution of a chiral auxiliary, a hydroxy group, and a sulfinyl group.