Abstract Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11–13, 24, and 25 using the chiral borane reagent chlorodiisopinocampheylborane [(I pc) 2 BCl]. Nickel (0)-mediated coupling of bromopyridines 2, 15, and 31 gives C 2-symmetric 2, 2′-bipyridines (R, R)- 32,(R, R′)-33, and (S, S)-38, respectively, which form metal complexes with Co II, Pd II, ...