Preheat oven to 450°. In a large bowl, whisk oil, syrup, salt, and pepper to blend. Trim brussels sprouts at base and remove any leathery outer leaves. Toss sprouts in oil mixture to coat well. Line a rimmed baking pan with foil and put sprouts in pan in a single layer.
Roast, tossing every 5 minutes, until sprouts are browned but tender-crisp, 10 to 12 minutes total. Remove from oven and let cool 10 minutes.
Meanwhile, cut each prosciutto slice into strips about 1 in. wide. Gently wrap each sprout lengthwise in a prosciutto strip. Insert a toothpick into the base of each sprout. Serve at room temperature.
Make ahead: Prepare through step 2 up to 1 day ahead; chill, covered. Bring to room temperature, then proceed.
Note: Nutritional analysis is per 2-skewer serving.
These are very good. We did some "test kitchen" with our batch to find the preferred way to prepare and serve. I roasted the brussel sprouts for 15 mins, and they were perfectly cooked through - browned on outside with some subtle crunch inside. We tried both room temp and "crisped" prosciutto and liked them better after 5 mins in a 350 degree oven to crisp prosciutto and serve warm. Serving with balsamic vinegar reduction drizzled on top / for dipping added an important additional dimension - wouldn't serve without. Had chili oil (olive oil to which crushed red pepper is added while warm then cooled) on hand as well - also very good drizzled over.
I love Brussels sprouts, and this is a fun way to present them. These were really good! Presentation was beautiful and fun, too, with colored toothpicks. I took another reviewer's suggestion and put them back in the oven for another five minutes after wrapping them in prosciutto. I made a batch and a half, and they went fast at my cocktail party. So easy and delicious! Got a lot of compliments. Will make these often.
The changes I made were spot on! I boiled the sprouts for 20 minutes - I like them soft and sweet. I doubled the sauce and the proscitto. Toss cooled, boiled sprouts in sauce, then wrap with plenty of prosciutto. Put in oven to bake and let the meat get crispy, then skewer. Yum!