Heat olive oil in a large pot or Dutch oven over medium heat. Add shallots, salt, and chile flakes and cook, stirring occasionally until shallots are tender but not browned, about 7 minutes.
Add tomato paste and cook, stirring the tomato paste into the shallots until it is melted and has turned from bright red to a brownish color, about 3 minutes. Add crushed tomatoes and oregano and reduce heat to low. Cook, uncovered, stirring frequently, until the sauce is thick and the flavors have melded, about 30 minutes. The sauce should be barely simmering. It will be very thick, almost a paste. This is fine, it will turn back into a sauce when you add the vodka and cream.
Meanwhile bring a large pot of heavily salted water to a boil. Once boiling add the pasta and cook about 1-2 minutes shy of al dente. Save about a cup of the pasta water. Drain pasta.
Once pasta is cooked and the sauce is thick, stir the vodka and cream into the sauce. Taste and add more salt and chile flakes if needed.
Add the pasta to the sauce and cook over low heat, stirring until the pasta is well coated and everything is warm. Add a bit of the reserved pasta water a little at a time if it seems too thick.
Spoon the pasta into bowls and sprinkle with parmesan and basil leaves.