Preheat oven to 375°.
Cover a baking sheet with parchment paper; secure to baking sheet with masking tape.
Melt butter in a medium nonstick skillet over medium heat. Add pear and pecans; sauté 2 minutes. Add the bourbon, syrup, and 1/4 teaspoon cinnamon; reduce heat, and simmer 5 minutes. Cool.
Cut about 1/2 inch from the tops and bottoms of apples, and discard. Core apples three-fourths of the way through from the top using a melon baller. (Do not cut through the bottom.) Fill each apple with 1 tablespoon pear mixture. Set aside the remaining pear mixture.
Place 1 phyllo sheet on a large cutting board or work surface (cover remaining dough to keep from drying); lightly coat with cooking spray. Place 1 apple in center of phyllo; overlap diagonal corners on top of the apple. Place on prepared pan, and coat phyllo with cooking spray. Repeat procedure with remaining apples and phyllo.
Combine 1/4 teaspoon cinnamon and sugar in a small bowl, and sprinkle over apples. Bake at 375° for 30 minutes or until the apples are golden brown. Spoon 1/4 cup remaining pear mixture around each apple; top each serving with 1/4 cup whipped topping. Garnish with mint sprigs, if desired.
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