Season the chicken with salt and pepper. Sprinkle with Italian seasoning. Place the flour in a shallow bowl and dredge the chicken through the flour, pressing to adhere. Heat 1 tablespoon olive oil in a large skillet set over medium-high heat. Add the prosciutto and cook until crispy all over, about 5 minutes. Remove from the skillet. In the same skillet, add 1 tablespoon olive oil and the chicken and sear on both sides until golden, about 3-5 minutes per side. Remove from the skillet. Add the shallots and garlic and cook until fragrant, 2 minutes. Stir in the sun-dried tomatoes, Italian seasoning, and a pinch each of red pepper flakes, salt, and pepper. Cook 2 minutes. Pour in the broth. Add the potatoes and chicken. Partially cover and cook over medium heat until the potatoes are fork tender, 10-15 minutes. Remove the lid. Pour in the cream. Add the dijon, lemon juice, parmesan, and Tuscan kale. Cook until the kale is wilted, 5 minutes. Serve the chicken and sauce with crispy prosciutto and fresh basil.