Categories: C-Si Bond Formation > Silanes
Synthesis of propargylsilanes
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Chiral spiro phosphate dirhodium complexes catalyze an asymmetric insertion
of alkynyl carbenes derived from readily available sulfonylhydrazones into the
Si-H bonds of silanes to afford various chiral propargylsilanes with excellent
enantioselectivity. Subsequently, a platinum catalyst was used for
stereospecific isomerization of the chiral propargylsilanes to the corresponding
chiral allenylsilanes.
L. L. Yang, J. Ouyang, H.-N. Zou, S.-F. Zhu, Q.-L. Zhou, J. Am. Chem. Soc.,
2021, 143, 6401-6406.
A copper-catalyzed deconjugative addition of silicon nucleophiles to a broad
range of enyne-type α,β,γ,δ-unsaturated acceptors provides α-chiral propargylic silanes with excellent enantiomeric
excesses. The method is 1,4-selective with hardly any formation of the
1,6-adduct. The double-bond geometry is shown to be critical for achieving this
chemoselectivity.
W. Mao, M. Oestreich,
Org. Lett., 2020, 22, 8096-8100.