Purée 2 1/2 cups tomatoes, wine, and garlic in blender. Heat oil in heavy large skillet over medium-high heat. Add tomato puree and olives. Cook until sauce begins to thicken, stirring often, about 6 minutes.
Meanwhile, cook pasta in large pot of boiling salted water until just tender but still firm to bite. Drain, reserving 1/2 cup pasta cooking liquid.
Add pasta, parsley, basil, and vinegar to sauce in skillet. Toss over mediumhigh heat until sauce coats pasta, adding reserved cooking liquid by 1/4 cupfuls if dry, about 3 minutes. Season to taste with salt and pepper. Mix in remaining 1 cup tomatoes and half of cheese. Mound pasta in bowl. Sprinkle with remaining cheese.
