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Copper-Catalyzed Asymmetric Hydroboration of α‑Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β‑Hydroxy-α-amino Acids

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journal contribution
posted on 07.03.2014, 00:00 by Zhi-Tao He, Yi-Shuang Zhao, Ping Tian, Chuan-Chuan Wang, Han-Qing Dong, Guo-Qiang Lin
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.