Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

Abstract

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E-selectivity.

Key words

quinone imine ketals - allenoates - [2+2] cycloaddition - E-selectivity

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