Abstract
Novel C 2-symmetric bis-sulfoxide/ N-oxide ( R, R)- 5 was prepared in good yield according to the Andersen protocol with ( S)-menthyl p-tolyl sulfinate (2 equiv) and the dilithium derivate of 2,6-dimethylpyridine N-oxide. Reduction of ( R, R)- 5 to pyridine/bis-sulfoxide ( R, R)- 6 was accomplished by means of Katritzky’s procedure (Fe 0/AcOH). Both bis-sulfoxides ( R, R)- 5 and ( R, R)- 6 are efficient chiral organocatalysts in the asymmetric allylation of N-benzoyl hydrazones derived from both aldehydes and ketones.
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