Nazarov Reactions of Vinyl Cyclopropylamines: An Approach to the Imino-Nazarov Problem
journal contributionposted on 07.06.2013 by Sara A. Bonderoff, Tina N. Grant, F. G. West, Martin Tremblay
Any type of content formally published in an academic journal, usually following a peer-review process.
Dichlorocyclopropanation of 2-amino-1,3-dienes affords 1-alkenyl-1-amino-2,2-dichlorocyclopropanes which undergo silver-assisted 2-π electrocyclic opening to furnish 3-aminopentadienyl cations. Nazarov-type cyclization of these intermediates leads to cyclopentenone iminium salts, which provide allylic amines upon reduction. This process, the imino version of the traditional Nazarov reaction, can also be combined with an interrupted Nazarov domino process to give polycyclic amines.