In a large pot over medium heat, warm olive oil. Add shallots and cook, stirring occasionally, until softened, about 5 minutes. Add garlic cloves and cook for one minute. Stir in whole tomatoes, chicken broth, and basil. Bring the mixture to a boil for 1 minute, then reduce the heat and simmer for 10 minutes.
Remove the soup from the heat and use a hand blender to puree it until smooth. Return the soup to the heat and add ravioli. Simmer until the pasta is cooked through, about 8 minutes. Stir in sugar and balsamic vinegar. Season with salt and pepper to taste.