Enantioselective Synthesis of α‑Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2‑Amino-1,3-diols

The
enantioselective copper-catalyzed oxidative desymmetrization
for the synthesis of chiral α-substituted serine derivatives
is reported. The combination of Cu­(OTf)2/(R,R)-PhBOX catalyst system, N-bromosuccinimide,
and MeOH enables us to provide chiral α-substituted serines
from N-2-methylbenzoyl-protected 2-amino-1,3-diols
through a simple procedure at room temperature under an air atmosphere.
A variety of α-substituent including aryl and heteroaryl groups
were tolerated in this method, and the corresponding chiral serine
derivatives were obtained in good to high yields with high enantioselectivities.