Recent progress in transition-metal-free functionalization of allenamides

Abstract

With their unique reactivity, selectivity, availability and stability, allenamides are receiving increasing attention, and reports on the functionalization of allenamides are rapidly growing in number. In this review, recent developments in transition-metal-free functionalization of allenamides are highlighted. First, developments based on allenamide reactivity are simply introduced. After presenting the advantages of allenamides, recent progress in transition-metal-free functionalization of allenamides is classified and discussed in detail in four parts: chiral phosphoric-acid-catalyzed asymmetric functionalization, iodine-reagent-mediated functionalization, 1,3-H-shift reaction of allenamides, and other metal-free allenamide functionalizations. For the majority of these transformations, plausible mechanisms are presented in detail. The purpose of this review is to provide illustrations of elegant allenamide chemistry, and thereby elicit further interest from the synthetic community to develop novel allenamide methodology.