No, this will not work. Generally speaking, dirsync is not supported for Cutover migration. The reason being, Cutover provisions accounts differently. As in, Cutover uses its own provisioning mechanisms and if an account already exists, it will throw an error. Also, the provisioning is based on a different attribute (mail/WindowsEmailAddress), compared to what dirsync uses, and can again cause troubles.
The "correct" way to do this is preform the cutover first, and only enable dirsync after the migration has been completed.