You need a router or other L3 device to do the routing. You could do some Policy-Based Routing to make the decision for Proxy/No Proxy depending on the port and destination address.
The clients may need to have their computers/devices set to point to the proxy (depending on the proxy and how you have it set up).
There are "Captive Portal" systems that will intercept all new connections for authentication, but I'm not sure that you can have them route to a specific interface once the authentication has been accomplished.
Cisco's Captive Portal is "BBSM," there are some other Open-Source systems .... hit Google for "nocat" or "captive portal" to get the list.
Good Luck
Scott