The efficient generation of multi-functional compounds in a single synthetic operation is a valuable tool in organic chemistry. It has been shown that symmetrical cycloalkanes can be ozonolyzed in the presence of saturated alcohols (e.g., methanol, ethanol, etc.) to generate aldehyde-alkoxy hydroperoxides. This reaction occurs via nucleophilic addition of the alcohol to the carbonyl oxide. The resulting hydroperoxide is then dehydrated to generate unsymmetrical aldehyde-ester products. We show how this powerful methodology can be extended to include the use of unsaturated alcohols as the nucleophile to generate aldehyde-ester-alkene compounds. We will report on the successful use of a variety of unsaturated alcohols and cyclic alkenes to generate versatile building blocks that have a variety of applications.

Ozonolysis of cycloalkenes in the presence of unsaturated nucleophiles: Synthesis of tri-functional aldehyde-ester-alkene compounds

253rd National Meeting (2017)

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