Catalytic Regio- and Enantioselective Alkylation of Conjugated Dienyl Amides

Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13547-13550. doi: 10.1002/anie.201808392. Epub 2018 Sep 17.


A method for catalytic asymmetric alkylation of conjugated dienyl amides has been developed and it allows efficient and high-yielding transformations of a wide range of polyconjugated amides into the corresponding chiral products. Smooth addition of organomagnesium reagents to relatively unreactive dienyl amides with excellent 1,6- and 1,4-selectivities, as well as enantioselectivites above 90 %, is achieved owing to the complementary action of the Lewis acid and a chiral copper-based catalyst.

Keywords: Lewis acids; asymmetric catalysis; conjugation; copper; regioselectivity.