Anti-Markovnikov addition of HCl
One way to do it would be do first do a hydroboration-oxidation reaction, which leads to the anti-Markovnikov addition of $\ce{H2O}$. So you will get an $\ce{-OH}$ group instead of $\ce{-Cl}$. Then, we can replace the $\ce{-OH}$ group with $\ce{-Cl}$ by treating it with $\ce{PCl3}$ or $\ce{PCl5}$.