Actually dielectric grease is often & usually of a silicone base. If you slather silicone inside an expensive adhesive lined heat shrink connector you will defeat the entire purpose of the adhesive lining as it will NOT adhere to silicone or grease and will make the added expense of the adhesive connector null and void. Remember NOTHING sticks to silicone not even new silicone. Adhesive lined heat shrink will NOT adhere to silicone dielectric grease!
Dielectric compounds are a nonconducting substance or an insulator by definition. I have often seen folks put dielectric compounds in the crimped connection itself.

Wrong! This will and can severely reduce the electrical quality of the crimped connection and can actually lead to resistance. Remember dielectric grease is an insulator or conductivity eliminator and NOT a conductivity enhancer..
If you want to use a dielectric grease with NON adhesive lined heat shrink that is a better match but do so ONLY after you have made the crimp. Because of dielectric greases properties you may never get the heat shrink to stay in one place and it can move and slide around on top of the dielectric grease..
If using adhesive lined heat shrink connectors do not use a dielectric grease. Using a Dielectric grease with an adhesive line heat shrink tube is totally defeating the purpose of the adhesive.
Sometimes more is not always better....