Assuming you have multiple IP's on your box you can make it work.
I used an apache server to proxy to two separate orion servers in a similar manner. In my httpd.conf I redirected to https from htpp.
<VirtualHost 192.168.174.101:80>
ServerName site1.domain.com
RewriteEngine On
RewriteCond %{SERVER_PORT} !^443$
RewriteRule ^/(.*)
[L,R,NC]
</VirtualHost>
<VirtualHost 192.168.174.102:80>
ServerName site2.domain.com
RewriteEngine On
RewriteCond %{SERVER_PORT} !^443$
RewriteRule ^/(.*)
[L,R,NC]
</VirtualHost>
then in my ssl.conf I had something like this;
<VirtualHost 192.168.174.101:443>
ServerName site1.domain.com
SSLEngine On
SSLCertificateFile conf/ssl/site1/site1.cer
SSLCertificateKeyFile conf/ssl/site1/site1.key
ProxyVia On
ProxyPass /
ProxyPassReverse /
</VirtualHost>
<VirtualHost 192.168.174.102:443>
ServerName site2.domain.com
SSLEngine On
SSLCertificateFile conf/ssl/site2/site2.cer
SSLCertificateKeyFile conf/ssl/site2/site2.key
ProxyVia On
ProxyPass /
ProxyPassReverse /
</VirtualHost>
Using a specific IP for each virtual host while including the ServerName directive seems to solve the problem of needing a unique IP but only being able to get a cert tied to a domain name. You could also use the same IP but with different ports, SSL only cares that it is a unique IP/Port combination. Hope this helps some.
Note: IP addresses were changed to protect the innocent. ;-)