title: Diethyl Phosphite Initiated Coupling of α-Ketoesters with Imines for Synthesis of α-Phosphonyloxy-β-amino Acid Derivatives and Aziridine-2-carboxylates.
abstract: Coupling of α-ketoesters with imines initiated by diethyl phosphite in the presence of alkaline metal hexamethyldisilazides is reported. Base-promoted addition of diethyl phosphite to α-ketoesters, followed by [1,2]-phosphonate/phosphate rearrangement, generates α-phosphonyloxy enolates that are subsequently intercepted by imines. The use of suitable azomethine coupling partners allows selective construction of syn-α-hydroxy-β-amino acid derivatives or trans-aziridine-2-carboxylates in high yields with excellent diastereoselectivities.
authors: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences and University of the Chinese Academy of Sciences , Urumqi 830011, China.
authors: Jin
authors: J
authors: Jiang
authors: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences and University of the Chinese Academy of Sciences , Urumqi 830011, China.
authors: Hui
authors: H
authors: Liu
authors: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences and University of the Chinese Academy of Sciences , Urumqi 830011, China.
authors: Chong-Dao
authors: CD
authors: Lu
authors: The Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences and University of the Chinese Academy of Sciences , Urumqi 830011, China.
authors: Yan-Jun
authors: YJ
authors: Xu