Synthesis of α-Aryl Amino Acids via Sommelet-Hauser Rearrangement

Significance

The methodology expands the synthetic utility of the Sommelet-Hauser (SH) rearrangement. It is noteworthy for its operational simplicity as well as for its unprecedented selectivity for the [2,3]- vs [1,2]-rearrangement. Now, sterically hindered α-aryl amino acids can be prepared efficiently with high stereoselectivity. Importantly, the authors reported that both Stevens- and SH-rearranged products 4 and 6 can be accessed by a simple change in base and solvent.