Synthesis of Chiral β‑Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation

The highly efficient Ni-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters was successfully developed using (S,S)-Ph-BPE as the ligand. A series of chiral β-borylated carboxylic esters were obtained with high yields (94%–99% yields) and excellent enan...

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Bibliographic Details
Published in:Organic letters 2019-06, Vol.21 (11), p.3923-3926
Main Authors: Han, Zhengyu, Liu, Gang, Zhang, Xianghe, Li, Anqi, Dong, Xiu-Qin, Zhang, Xumu
Format: Article
Language:English
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Summary:The highly efficient Ni-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters was successfully developed using (S,S)-Ph-BPE as the ligand. A series of chiral β-borylated carboxylic esters were obtained with high yields (94%–99% yields) and excellent enantioselectivities (89%–99% ee). The gram-scale asymmetric hydrogenation with a low catalyst loading (0.25 mol %) and synthetic transformation of hydrogenation product demonstrated the great synthetic utility of this methodology.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00994