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Bring a large pot of salted water to a boil. Cook the pasta al dente, according to package directions. During the last 2-3 minutes of cooking add the asparagus. Drain.
In a large skillet, toss together the chicken, with the olive oil, Italian seasoning, and a big pinch of pepper. Add 2 tablespoons butter, then set over medium-high heat. Cook the chicken until crisp, about 5-8 minutes. Stir in 2 tablespoons of pesto, then cook another 2 minutes. Add the prosciutto to the pan and cook 1 minute to warm through. Turn the heat off and transfer everything to a plate.
To the same pan, add 2 tablespoons butter, the garlic, and chili flakes. Cook 1 minute, until fragrant, then pour in the broth and milk. Whisk until smooth. Bring the sauce to a gentle simmer and cook 5 minutes, until slightly thickened. Stir in the remaining pesto and the parmesan, then toss in the pasta and asparagus. Cook 2 minutes. Stir in the chicken. Remove from the heat and top with fresh basil.
Serve immediately topped with prosciutto and greens.