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1
Combine 2 cups of the pineapple, the sugar, vinegar, soy sauce, and garlic in a blender and blend on high until smooth, about 30 seconds.
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2
Pour into a medium saucepan and bring to a boil over medium heat.
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3
Skim off any foam and reduce heat to low.
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4
Simmer until glaze is thick and syrupy enough to coat the back of a spoon and has reduced to about 3/4 cup, about 30 minutes.
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5
Stir in cayenne and set aside to cool slightly, at least 5 minutes. Meanwhile, heat a gas or charcoal grill to high (about 400u00b0F) or a grill pan over high heat until very hot.
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6
Skewer 1 shrimp, making sure to pass the skewer through the thick portion and the tail portion, then skewer 1 piece of the remaining pineapple. Repeat, alternating between the two and leaving a space in between, until you have 3 shrimp and 2 pineapple pieces per skewer. Brush skewers on one side with glaze.
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7
Rub the grill with a towel dipped in vegetable oil, place the skewers on the grill glaze side down, and brush the other side of the skewers with more glaze.
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8
Continue brushing and turning every few minutes until the thick portions of the shrimp are white and firm, about 10 to 15 minutes.
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9
Remove from the grill and serve immediately.
