Studies towards the Enantioselective Synthesis of Cryptowolinol via Pd 0 -Catalyzed C(sp 3 )-H Arylation/Parallel Kinetic Resolution.

We report a model study towards the enantioselective synthesis of the dibenzopyrrocoline alkaloid (-)-cryptowolinol. The key step involves a challenging enantioselective Pd 0 -catalyzed C(sp 3 )-H arylation performed with a chiral NHC ligand, which proceeds via parallel kinetic resolution (PKR). A very efficient PKR process was achieved on a deoxygenated model substrate and was successfully transposed to a potential intermediate en route to (-)-cryptowolinol.