It seems the checkbox configuration is integrated in JIRA (at least in 3.6.2) for reports and works fine.
Unfortunately there is a bug in objectconfiguration_form.jsp in the 'checkbox part'. The name and value of the checkbox are print out using
<webwork:property value="." />
<webwork:property value="paramValue(.)" />
, probably left over from debugging !?

Also when trying to use the checkbox in a portlet configuration, an error occurs, that the type is not supported.
The handling for the checkbox is missing the the class AbstractSaveConfiguration, method syncPropertySetToParams.