Resposta curta
Não, não tente o que você está perguntando, pensando ou considerando.
Resposta longa
Leia as Perguntas frequentes: 5.1 Tenho muitos aplicativos já instalados no Windows. Como faço para executá-los no Wine? , que afirma:
Wine is not designed to interact with an existing Windows installation. If you have any data you need from a Windows installation, browse your Windows filesystems in your normal file manager and copy the data to another location.
E depois continua:
Do not try to configure Wine to point to your actual Windows C:\ drive. This will break Windows and require a Windows reinstall. We have tried to make this hard to do, so you probably cannot do it by accident. If you do manage this, Wine may or may not continue to operate, but your Windows install will be 100% dead due to critical parts of it being overwritten. The only way to fix Windows after this has happened is to reinstall it.