Abstract Addition of allyl halides to the organolithium species derived from lithiation of N-tert- butoxycarbonylindoline with sec-butyllithium (sec-BuLi) and tetramethylethylenediamine (TMEDA) occurs regioselectively by SN 2 allylation. In contrast, the organolithium species can be transmetalated to the mixed zinc cuprate that undergoes regioselective SN 2′ allylations. Transmetalation to the organozinc chloride allows a Negishi-type cross- ...