Biomimetic Polyene Cyclizations. Asymmetric Induction during the Acid-Catalyzed Cyclization of Chiral Imines

Article abstract of DOI:10.1021/jo00328a023

This paper reports the details of a basic study showing that an imino function is suitable to initiate acid-catalyzed cyclizations of polyenes, affording high yields of cyclized products.The additional advantage of such a function is to introduce very easily a chirality on the polyene skeleton by the way of a chiral group linked to nitrogen.The extent of asymmetric induction by a chiral phenethyl group on nitrogen is from 36percent to 65percent, according to the monocyclic or bicyclic nature of the substrate.