Construction of the Erythrinane Core Skeleton via Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Zhen, LiTong, ShuoZhu, JiepingWang, Mei-Xiang2020-11-152020-11-152020-11-15202010.1021/acs.joc.0c01992https://infoscience.epfl.ch/handle/20.500.14299/173380We report herein an efficient cascade strategy for the rapid construction of a highly enantioenriched erythrinane core skeleton. Under the sequential catalysis of a chiral Cr(III)(salen)Cl and InCl3, cyclohexanone-derived tertiary enamides undergo an intramolecular enantioselective nucleophilic addition followed by diastereoselective Pictet−Spengler cyclization. This method is highly enantio- and diastereoselective, leading to diverse erythrina alkaloid derivatives as the sole diastereoisomer with up to 98% ee.Construction of the Erythrinane Core Skeleton via Asymmetric Catalytic Cascade Reaction of Tertiary Enamidestext::journal::journal article::research article