I assume you mean one side fully covered with fins, the other side completely flat.
The angle bracket solution can work, but it introduces additional thermal resistance between the TO-3 and the heatsink, and hence gives greater die temperature for a given power dissipation. Depending on the situation this may become a problem.
A suitably thick custom drilled bracket, additional mounting screws, extra heat transfer compound, assembly, etc will probably cost more than the savings made in the heat sink.
I've seen it done, and done it myself, when mechanical constraints overrode the additional costs involved.
Preference should be with a heat sink designed for TO-3's if possible