title: Copper-catalyzed asymmetric hydroboration of α-dehydroamino acid derivatives: facile synthesis of chiral β-hydroxy-α-amino acids.
abstract: The Cu-catalyzed asymmetric conjugate hydroboration reaction of β-substituted α-dehydroamino acid derivatives has been established, affording enantioenriched syn- and anti-β-boronate-α-amino acid derivatives with excellent combined yields (83-99%, dr ≈ 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable β-hydroxy-α-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive molecules.
authors: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors: Zhi-Tao
authors: ZT
authors: He
authors: Yi-Shuang
authors: YS
authors: Zhao
authors: Ping
authors: P
authors: Tian
authors: Chuan-Chuan
authors: CC
authors: Wang
authors: Han-Qing
authors: HQ
authors: Dong
authors: Guo-Qiang
authors: GQ
authors: Lin
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003300:Copper