Prepare grill to medium-high.
Sprinkle steak with rosemary, pepper, and kosher salt. Place steak on grill rack coated with cooking spray; grill 7 minutes on each side or until desired degree of doneness. Remove from grill; let stand 10 minutes. Cover and keep warm.
While steak rests, heat oil in a small saucepan over medium-high heat. Add shallots; sauté 1 minute. Add tomato paste; cook 1 minute. Stir in broth and sugar. Bring to a boil; cook 3 minutes or until thickened. Remove from heat; stir in bourbon, vinegar, and 1/8 teaspoon salt. Cut steak diagonally across grain into thin slices. Serve with sauce.