I think on the Mac the best you can do is "VPN on Demand"
On the Mac go to, System Prefs, Network, find your VPN connection, click the "Advanced" button, and select the "VPN on Demand" tab, and select the domain that the user is trying to connect to (corporatedomain.local or corporatedomain.com) then the VPN will kick in when a user tries to access anything that ought to be on the corporate network.
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by: thinkpads_userPosted on 2009-08-28 at 15:18:17ID: 25212004
I depends entirely on the client application. Check the application for "Manually connect" and disable, or "Start with OS startup" and see if that will cause it to start up.
Remember that if the VPN starts within the office environment (where the VPN connects to), it may cause an inability to connect to anything. Generally, in my own experience, it is better not to connect automatically, but that is only from my own perspective.
... Thinkpads_User