UPDATE: Solution right after question.
Usually, synchronization is serializing parallel requests within a JVM, e.
In general, don't rely on HttpServletRequest.getSession() returning same object. It's easy for servlet filters to create a wrapper around session for whatever reason. Your code will only see this wrapper, and it will be different object on each request. Put some shared lock into the session itself. (Too bad there is no putIfAbsent though).