As part of a programme to examine new catalytic asymmetric routes to dihydropyridones of type 4,   we were examining an alternative to the formal aza-Diels-Alder approach, i.e. via a direct route using enone derivatives 6  in place of dienes 2  by using a Mannich-Michael pathway.[1] This led to the discovery of two novel reactions: formal [2+2+2]- and  [1+2+1+2]-cycloadditions to form dihydropyridine derivatives 7  and 8  respectively.  This presentation will discuss possible mechanisms and reasons for these different reactions. [1]Girling, P. R.; Kiyoi, T.; Whiting, A. Org. Biomol. Chem., 2011  , 96, 3105.

Novel routes to dihydropyridine systems

243rd National Meeting (2012)

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