Chiral enamides are valuable and versatile structual motifs in natural products and active drugs as they present a convenient entry towards nitrogen-containing target molecules. However, methodologies to synthesize chiral enamides, especially with a remote γ-stereocenter, remains particularly challenging, thus new strategies to construct such moieties are highly desirable. As a result, our group is utilizing an organocatalytic method to stereospecifically isomerize α-chiral allylic amines and subsequently react them with various benzoyl chlorides in a one-pot fashion to access γ-chiral enamides. This approch produces high yields, high enantiomeric excess as well as high levels of chirality transfer with a wide scope of benzoyl chlorides and electronic variations within the substrate. Additionally, a gram-scale reaction demonstrates the synthetic applicability of this procedure. Furthermore, different applications of the γ-chiral enamides are described to access other interesting moieties.

Stereospecific isomerization towards γ-chiral enamides

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