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I honestly don't know if using a single key for a shortcut is even supported. It will probably only work until another program restores the key's normal function. At which point you'd probably have to close all running programs and relaunch Sigil to achieve the effect you want. It's not a bug, but rather, it's something that's just not feasible. You'd probably need to look for some sort of low-level keyboard-mapping software to pull something like that off.
It's another reason why entering text via Sigil is just not the way to go. Most word-processing programs already have the ability to convert straight-quotes to curly ones "on the fly."
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