Heat 4 tablespoons of the oil in a large saucepan or Dutch oven over medium high heat. Add the shallots and onion and sweat until light brown, then add garlic and sweat another 3 minutes.
Add the wine and reduce by half. Add the stock, canned tomatoes with juices, thyme and bay leaves to pan. Simmer uncovered for 45 minutes.
Meanwhile, saute the fresh tomatoes in remaining 1 tablespoon oil for 2 minutes and set aside. Remove thyme sprigs and bay leaves from soup and puree soup in a blender. Stir in the sugar, lemon juice, 1 1/2 cups of the cream, salt and pepper. Return soup to saucepan and stir in Sauteed tomatoes, mint and chives. Gently warm soup over medium heat.
Meanwhile, whip remaining 1/2 cup of cream to soft peak and fold in grated Parmesan cheese if desired.
To serve, ladle soup into bowls, garnish with a dollop of whipped cream.
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