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.
A copper-catalyzed electrophilic amination of gem-diborylalkanes with hydroxylamines has been developed. The key to its success is the use of the Me 3 Si-modified 1,2bis(diphenylphosphino)benzene ligand. Additionally, the reactivity of neopentylglycol derivatives compared to that of commonly used pinacol-derived ones is found to be higher, particularly in the case of relatively sterically congested substrates. The copper catalysis presented here enables the first successful catalytic carbon−heteroatom bond forming reaction of gem-diborylalkanes to form the corresponding αaminoboronic acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry.
A copper-catalysed regio- and stereoselective hydroamination of acrylates with hydrosilanes and hydroxylamines has been developed to afford the corresponding α-amino acids in good yields. The key to regioselectivity control is...
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).
A copper-catalysed regio- and diastereoselective borylamination of α,β-unsaturated esters with B2pin2 and hydroxylamines has been developed to deliver the acyclic β-boryl-α-amino acid derivatives with high anti-diastereoselectivity (up to >99:1), which...
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