Why not compute the file hash on your local machine before encryption, and check that hash against a master dupe list (hash, dupe_count) of all hashes from all users' pre-encrypted local files?
Secondly, I cannot see how this requires there to be an index of users hashes. Surely one could store hashes with reference count, increment when a user adds, decrement when a user deletes. The user ID isn't necessary for a reference counter.
Not saying Dropbox isn't doing what he says. But he says de-duping proves they can decrypt and proves they have a list of who has the same files. I don't see it from de-dupe alone.