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Firstly the option in question is "Sync from shelves". That is only one way, it's in the name, "from". If it was "with", it would probably be two-way. There are separate options for going the other direction.
Most of the sync shelves is about matching with existing books. It matches using the Goodreads ID. It doesn't attempt to match on anything else as there is no guarantee it will work. But, in the result window if you right click on a book that has the status "No calibre book linked!", there are options to search calibre for a book or to add an empty book. If you use the add empty book option, all the books will be created with the title and author and GR id. If you want more metadata or covers, then you need to run a metadata download for the books.
If you used the Import List plugin to add the books from a list exported from GR, you should have been able to include the GR id. That should have let the sync match the books.
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