If your Mac is running MS Office for Mac 2011, to enable automatic sync of Address Book (Contacts), iCal (events and To Dos/Reminders) and Mail notes (for Mac OS X 10.6.6-10.7.x) with MS Outlook, the following boxes should be ticked in Sync Services (go to Preferences of MS Outlook 2011):
Also, please, note that in MS Outlook the categories list displays categories created for all the four groups (Calendar, Contacts, Tasks, Notes). So, no matter what you sync – Contacts, iCal events or To Dos/Reminders, new categories will appear in the general list of categories.
If your Mac is running MS Office for Mac 2011, Entourage notes plugin is SyncMate will be disabled. It is caused by the fact that MS Entourage is replaced with MS Outlook in MS Office for Mac 2011.