Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol

A convenient route to a benzo-fused amino indanol chiral controller is disclosed. The synthesis is based on a newly optimized entry to 3H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl2-box complex shows preservation of the distorted square planar geometry found in the parent CuCl2(indanyl-box) despite greater steric crowding by the blocking groups.