1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane Periodate: a Mild and Efficient Oxidant for the Cleavage of Oxime Double Bonds under Anhydrous Conditions†

Abstract

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate (BAABCP) (1), readily prepared from commercially available 1,4-diazabicyclo[2.2.2]octane (DABCO) and sodium periodate, converts oximes and α-sulfinyl oximes to the corresponding carbonyl compounds and β-keto sulfoxides, respectively, in high yields and high enantiomeric purity.