Here's the relevant section of perlop:

If what's within the angle brackets is neither a filehandle nor a simple scalar variable containing a filehandle name, typeglob, or typeglob reference, it is interpreted as a filename pattern to be globbed, and either a list of filenames or the next filename in the list is returned, depending on context. This distinction is determined on syntactic grounds alone. That means <$x> is always a readline() from an indirect handle, but <$hash{key}> is always a glob(). That's because $x is a simple scalar variable, but $hash{key} is not--it's a hash element.

One level of double-quote interpretation is done first, but you can't say <$foo> because that's an indirect filehandle as explained in the previous paragraph. (In older versions of Perl, programmers would insert curly brackets to force interpretation as a filename glob: <${foo}> . These days, it's considered cleaner to call the internal function directly as glob($foo), which is probably the right way to have done it in the first place.)