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Catalytic Asymmetric Hydrogenation of (Z)-α-Dehydroamido Boronate Ester: A Direct Entry to Alkyl-substituted α-Amidoboronic Ester

Abstract

The direct catalytic asymmetric hydrogenation of (Z)-α-dehydroamino boronate ester was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic ester was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield, 99% ee). The utility of the product had been demonstrated by transformation to their corresponding boronic acid derivatives, Pd-catalyzed borylation reaction and an efficient synthesis of the potential intermediate of bortezomib. The clean, atom-economic and environment friendly process of this catalytic asymmetric hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic ester of great potential in the area of organic synthesis and medicinal chemistry.

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Publication details

The article was received on 07 Sep 2019, accepted on 21 Nov 2019 and first published on 25 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04534A
Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Catalytic Asymmetric Hydrogenation of (Z)-α-Dehydroamido Boronate Ester: A Direct Entry to Alkyl-substituted α-Amidoboronic Ester

    Y. Lou, J. Wang, G. Gong, F. Guan, J. Lu, J. Wen and X. zhang, Chem. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C9SC04534A

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