Synthesis of β‑Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters

A copper-catalyzed silylamination of α,β-unsaturated esters with silylboranes and hydroxylamines has been developed to afford the corresponding β-silyl-α-amino acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry. Additionally, by using a suitable chiral bisphosphi...

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Bibliographic Details
Published in:Organic letters 2022-02, Vol.24 (6), p.1418-1422
Main Authors: Kobayashi, Toshimichi, Nishino, Soshi, Miura, Masahiro, Hirano, Koji
Format: Article
Language:English
Subjects:
Amination
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Copper - chemistry
Esters - chemistry
Molecular Structure
Silicon Compounds - chemical synthesis
Silicon Compounds - chemistry
Stereoisomerism
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Summary:A copper-catalyzed silylamination of α,β-unsaturated esters with silylboranes and hydroxylamines has been developed to afford the corresponding β-silyl-α-amino acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry. Additionally, by using a suitable chiral bisphosphine ligand, the asymmetric induction is possible, delivering the optically active β-silyl-α-amino acids with synthetically acceptable diastereomeric ratios (55:45–82:18 dr) and high enantiomeric ratios (81:19–99:1 er).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00309