Simmer pineapple, 1/2 cup sugar, water, chili sauce, and lime juice in a saucepan over medium-high heat. Cook until thickened, 5–8 minutes. Puree until smooth; set aside.
Blend cream cheese, cilantro, scallion, ginger, sugar, jalapeño, and lime juice in a bowl; gently fold in crab.
Arrange wonton skins on a work surface. Place 1 teaspoon of crab mixture in center of each, then moisten edges with water. Fold to form a triangle, pressing to seal. Moisten the outer corners of the triangle, seal together to form a "hat," and place on a parchment-lined baking sheet. Heat oil to 350° in a pan over med.-high.
Fry wontons in batches until golden on both sides, 2 - 3 minutes total. Drain on paper towels; serve with pineapple sauce. Fry remaining wontons in the same way.