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Cu‐Catalyzed Reductive gem ‐Difunctionalization of Terminal Alkynes via Hydrosilylation/Hydroamination Cascade: Concise Synthesis of α‐Aminosilanes
Author(s) -
Nishino Soshi,
Hirano Koji,
Miura Masahiro
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001799
Subject(s) - hydroamination , hydrosilylation , chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , ligand (biochemistry) , enantiomer , optically active , cascade , cascade reaction , enantiomeric excess , organic chemistry , receptor , biochemistry , chromatography
A copper‐catalyzed reductive gem ‐difunctionalization of terminal alkynes with hydrosilanes and hydroxylamines has been developed. The reaction proceeds via hydrosilylation/hydroamination cascade, and the readily available and simple terminal alkynes can be transformed into the corresponding α‐aminosilanes of medicinal interest in a single operation. Additionally, the use of chiral bisphosphine ligand successfully makes the reaction enantioselective to deliver the optically active α‐aminosilanes with good enantiomeric ratios.