Its been tried before, not only C++ => C#, but VB6 => VB.NET, C++ => Java and any other old => new that you can think of. it never really worked. I think that because ppl don't consider that transformation for what it really is (a total rewrite) they tend to take it lightly.
The migration story from C++ => .NET should be thru CLI, carefully deciding what managed and whats remains unmanaged and s-l-o-w-l-y "fixing" piece by piece.