Add chopped pineapples to medium skillet over medium-high heat. Cook, stirring occasionally until liquid from pineapples evaporates and pineapples begin to brown, about 5 minutes. Stir in cream of coconut and sweetened condensed milk; bring to boil. Reduce heat to medium. Simmer, stirring occasionally, until coconut mixture reduces to thick syrup and turns light golden brown, 7-8 minutes. Stir in flaked coconut, vanilla extract and ground cinnamon. Transfer pineapple-coconut mixture to heat-proof bowl; let sit until steam subsides. Transfer to refrigerator; chill until cold. (Note: Filling can be stored covered in refrigerator for up to 1 week).
Heat oven to 425°F. On lightly floured work surface, using rolling pin, roll out puff pastry round until about ½” larger in diameter. Spoon 2 tbsp. cooled coconut-pineapple mixture into middle of dough. Moisten edges with beaten eggs and fold in half to form half-moon shape. Seal edges by pressing with fork; transfer to greased baking sheet. Repeat with remaining pastry rounds and filling to make 12 empanadas. Brush tops of empanadas with beaten egg; sprinkle with sugar.
Bake until empanadas are puffed and golden brown, about 20 minutes, rotating pan after 10 minutes for even browning. Transfer empanadas to cooling rack; let sit until cool enough to handle. Serve warm or at room temperature.