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Asymmetric Synthesis of Substituted Homotropinones from N-Sulfinyl β-Amino Ketone Ketals. (−)-Euphococcinine and (−)-Adaline

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journal contribution
posted on 19.02.2010, 00:00 by Franklin A. Davis, Ram Edupuganti
Sulfinimine-derived N-sulfinyl β-amino ketone ketals on heating with NH4OAc:HOAc undergo a four-step intramolecular Mannich cyclization cascade reaction to give homotropinones, such as (−)-euphococcinine, in excellent yields as single isomers.