If you boil bejebuz out of the wort to reduce it your not actually caramelising the wort your either burning it or just reducing it.
As long as the boil contains enough water to generate steam, the temperature won't rise much above 100C except for some of these odd browning reactions that occur at the interface of the wort and the kettle. Once most of the water is gone, the temperature rises sharply and pyrolysis starts to happen in a big way, and that is when most cooks would consider that they are making "caramel". One signal that this is all about to happen, as someone else mentioned, is that the wort foams up. Another signal of course is the increased viscosity.
It may well be that different sugars pyrolyse differently and at different rates, which could be a justification for using some acid to promote inversion of both sucrose and maltose. Note that inversion is actually a hydrolysis reaction, ie, it requires water. There is a school of thought that the heat is enough to make hydrolysis happen anyway (to some extent) without the presence of acid. And once the water becomes scarce it is possible that a dehydration reaction could reverse the hydrolysis.
One idea I have been tossing around for a while is to try and caramelise some dextrin (corn syrup) in a bid to replicate what might be going on during decoctions. Alternatively, I guess you could boil down some first runnings at an early stage of the mash, and hope not to deplete the enzyme content too much.