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Synthesis 2022; 54(08): 2049-2056
DOI: 10.1055/a-1701-7500
DOI: 10.1055/a-1701-7500
paper
Enantioselective, Copper-Catalyzed Addition of Nucleophilic Silicon to Alkenyl-Substituted Phosphine Oxides
W. M. thanks the China Scholarship Council for a predoctoral fellowship (2017–2021), and M.O. is indebted to the Einstein Foundation Berlin for an endowed professorship.
Abstract
An enantioselective β-silylation of α,β-unsaturated phosphine oxide derivatives using a silylboronic ester as the silicon pronucleophile is reported. The reaction is catalyzed by copper salts in the presence of chiral pyridine–oxazoline (PyOx) ligands. Good to high enantioselectivities (≤95% ee) are obtained for β-aryl-substituted acceptors whereas alkyl residues in the β-position led to a lower ee value for 1° and no reaction for 2° and 3°. The new method represents another way of accessing α-chiral silanes and complements the known β-borylation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1701-7500.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 02. November 2021
Angenommen: 19. November 2021
Accepted Manuscript online:
19. November 2021
Artikel online veröffentlicht:
20. Januar 2022
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For a recent Outlook, see:
NHC catalysis without a transition-metal catalyst:
See also: