Routing specific pages through port 443??

I assume you're applying this rule to an HTTP virtual server and only want to redirect the login requests to HTTPS (leaving the rest of the requests to be answered by the HTTP virtual server). If so, the first redirect for Login.asp/Login.jsp looks correct. However, it shouldn't be necessary to redirect the requests which don't match the Login pages. You should be able to just remove the else portion:

when HTTP_REQUEST {
   if { ([HTTP::uri] contains "Login.asp") or ([HTTP::uri] contains "Login.jsp") }{
      HTTP::redirect https://[getfield [HTTP::host] ":" 1][HTTP::uri]
   }
}

As long as you have a default pool configured on the virtual server, all non-Login requests will be sent to that pool

If you're unsure of how the traffic is being parsed, you can add logging statements to the rule:

log local0. "client: [IP::client_addr] requested URI: [HTTP::uri]"

Aaron