The discovery of the novel reactivity of conjugated enynes, mediated by readily available halogenation reagents, opens a broad range of mechanistically unique pathways for the synthesis of highly functionalized chiral allene derivatives. Bromoallenyl pyrrolidines can be synthesized via 1,4-addition of sulfonamide nitrogen nucleophiles and halogens to conjugated enynes. This process can lead to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under economical and environmentally friendly reaction conditions.