Gold‐Catalyzed Formal Dehydro‐Diels–Alder Reactions of Ene‐Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies

Abstract

A new protocol for the synthesis of a variety of N‐containing aromatic heterocycles by a formal gold‐catalyzed dehydro‐Diels–Alder reaction of ynamide derivatives has been developed. Deuterium‐labeling experiments and kinetic studies support the involvement of a dual gold catalysis mechanism in which a gold acetylide moiety adds onto an aurated keteneiminium.

Ring forming transformations of ynamides via cycloaddition

“…During the last decade, extensive work on ynamides revealed their attractive synthetic features and broad application spectrum that considerably stimulated the development of the asymmetric synthesis of Nheterocycles. [110][111][112][113][114][115][116][117][118] In addition to this, the synthetic applications of the developed methodologies for the total synthesis of natural products with biological and optoelectronic properties have been achieved. [119][120][121] Further the application of the transformations could be extended for the synthesis of biologically active and pharmaceutical molecules via late-stage functionalization.…”