The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96 : 4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97 : 3 selectivity in the absence of any additional chiral agents.
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Bower et al. (1996) studied this question.
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