In the presence of a chiral iridium complex, commercially available 3-chloro-2-chloromethyl-1-propene (1) was selectively activated for various reductive couplings. Depending on the reaction conditions it allows a selective mono- or bidirectional condensation with one or two external aldehydes with excellent enantiocontrol (>90% ee). This approach occurring simply under mild conditions and avoiding premetalated reagents constructs rapidly chiral homoallylic alcohols, key precursors of important molecular fragments such as furans, pyrans, ketodiols, or 1,3,5-polyols.