In situ generation of chiral N-dienyl lactams in a multicomponent reaction: An efficient and highly selective way to asymmetric amidocyclohexenes

Chiral N-dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports on a highly efficient and diastereoselective multicomponent methodology utilizing chiral amides, aldehydes, and dienophiles (AAD reaction). The three components readily react under in situ generation of chiral N-dienyl lactams which undergo a subsequent Diels-Alder reaction. Different chiral amides have been employed in the standard protocol delivering yields up to 94%, and selectivities up to 90% de. Moreover, DFT calculations were performed to explain the obtained selectivities.