Developed by Boaz and co-workers at the Eastman Chemical Company as a three step synthesis from PPFA. Applications that result in >80% ee are primarily in Rh catalysed hydrogenation, with one example of Ir catalysis. Literature covered until end 2019 (7 entries).
Rhodium
Rh – Hydrogenation OL02-4-2412 and JOC05-70-1872. See also TA05-16-2063.
OL07-9-4825 See corrigendum for correct assignment of absolute configuration.
The synthesis of the optimised (and not commercially available) ligand for this reaction is available here.
Absolute configuration not stated, but for the phenyl-substituted product tentatively assigned as R.
Absolute configuration of ligand and mol% loading of ligand and Rh complex not stated. Neither is the E/Z ratio of the substrate, the reaction temperature and time, and the intrinsic diastereoselectivity of the substrate (i.e. dr using an achiral catalyst).
Iridium
Ir – Hydrogenation TA08-19-938
