The synthesis of a second-generation -helicenoidal DMAP organocatalyst is reported. The synthesis is reliant upon a highly diastereoselective Rh-catalysed [2 + 2 + 2] triyne cycloisomerization, using an existing stereocentre to control the sense of forming helicity. Taken together, a scalable (>1 g), resolution-free entry to a helical DMAP with the capacity for subsequent functionalization, has been achieved.
Crittall, M. R., Fairhurst, N. W. G., & Carbery, D. R. (2012). Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst. Chemical Communications, 48(91), 11181-11183. https://doi.org/10.1039/c2cc35583c