3.5" Drives with enclosures generally come with their own PSU and have no problem working with the Raspberry pi. The problem children are the 2.5" drives that are powered from the USB only. My hub only supplies 500ma per port and works just fine with a USB to SATA adapter that includes a "Y" cable. It will not work directly from the RasPi at all, (I have occasionally got it to work but it does not last long) but it works on every hub I have tried so far.
I have even used it to provide the back-power to the RasPi. I plugged the Data/Power cable into the RasPi and then plugged the power only USB port into an iPad charger (5V 2.1A). Worked well, the only problem is there is no real overvoltage protection with that setup. There is a picture of it operating on my website if you do not happen to believe me.

Your adapter may be a little pickier or your HDD might draw a little too much for proper operation.
I have used mostly Seagate 120GB and 320GB laptop drives. My Lapdock uses a bone stock 640GB Free Agent with the supplied single cable and works like a charm. I also have used a Toshiba 1TB drive. I have used those hubs to run a USB DVD-RW (bought from Wal-Mart) drive that uses a single port USB cable with no problems.
None of my hubs supplied back-power from the manufacturer. I had to make them back-power. They worked with the USB HDD adapter either way. 1 stock and two modified to back-power (back-feed)
The USB to SATA adapter I am using is below;
http://www.newegg.com/Product/Product.a ... 6812816095
The hub is here;
http://www.newegg.com/Product/Product.a ... 6817111831
Its factory specs state it is for less than 500ma per port.
I hope this helps you out!