Preheat oven to 400°F. Cut the prosciutto slices longwise in half and wrap each asparagus. Place the asparagus on a baking sheet. Drizzle with olive oil and season with salt and pepper.
Bake for 20 minutes until the prosciutto is crisp and golden.
While the asparagus are baking, prepare the glaze. In a small saucepan, at medium heat, combine the balsamic vinegar and sugar until reduced to half. Drizzle over asparagus and serve immediately.