BoPhoz

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 2017 (7 entries).

BoPhoz

Rhodium

Rh – Hydrogenation OL02-4-2412 and JOC05-70-1872. See also TA05-16-2063.

PP-BoPhoz_OL02-4-2421

OL07-9-4825 See corrigendum for correct assignment of absolute configuration.

PP-BoPhoz_OL07_9_4825-1

JOC09-74-4408

PP-BoPhoz_JOC09-74-4408

The synthesis of the optimised (and not commercially available) ligand for this reaction is available here.

 JOC08-73-2302

PP-BoPhoz_JOC08-73-2302

TA08-19-1189

PP-BoPhoz_TA08-19-1189_1

Absolute configuration not stated, but for the phenyl-substituted product tentatively assigned as R.

BMCL16-26-5164

BoPhoz_JOC09-74-4408

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

PP-BoPhoz_TA08-19-938