An efficient radical cascade involving a 5-exo-dig, a 1, 6-H transfer, a 6-endo-trig, a 4-exo- dig, and a final 1, 6-H transfer allows the diastereoselective construction of bicyclo [3.1. 1] heptanes. The size of the R substituent at the propargylic position governs the diastereoselectivity of the 6-endo-trig step. Other parameters (acetylenic substituents, unsaturated partners,...) have been investigated, and the scope and the limitations of the ...