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

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journal contribution
posted on 11.03.2019, 14:19 by Kosuke Yamamoto, Shota Ishimaru, Tatsuya Oyama, Satoko Tanigawa, Masami Kuriyama, Osamu Onomura
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.