A Diastereoselective Assembly of Tetralone Derivatives via a Tandem Michael Reaction and ipso -Substitution of the Nitro Group.
Nicolai A AksenovDmitrii A AksenovDaniil D GanusenkoIgor A KurenkovAlexander V AksenovPublished in: The Journal of organic chemistry (2023)
A highly diastereoselective tandem reaction of 2'-nitrochalcones is reported, involving Michael addition and a subsequent ipso -substitution of the nitro group to produce 1-tetralones with two contiguous chiral centers. A related annulation reaction of 2'-nitrochalcones with potassium cyanide affording 1-indanones with a C3-quaternary chiral center is also demonstrated.