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Synthesis 2023; 55(06): 892-898
DOI: 10.1055/s-0042-1751386
DOI: 10.1055/s-0042-1751386
feature
Lewis Acid Catalysed Asymmetric One-Carbon Ring-Expansion of Prochiral Cyclobutanones
Generous financial support from the Johannes Gutenberg-Universität, the Westfälische Wilhelms-Universität, and the Fonds der Chemischen Industrie (Liebig fellowship to J.M.W. & Liebig-Ph.D. fellowship to M.T.) is acknowledged.
Abstract
Enantioselective methylene insertion into prochiral cyclobutanones is described providing access to chiral β-substituted cyclopentanones as important structural motif in synthesis and natural products. Commercially available trimethylsilyl as well as other silyl diazomethanes act as one-carbon synthon and scandium triflate is found to be a potent Lewis acid catalyst. By using bis(oxazoline) ligands, enantioinduction is achieved for a number of β-substituted cyclopentanones including examples bearing all-carbon quaternary stereocentres.
Key words
desymmetrisation - ring expansion - prochiral cyclobutanones - chiral cyclopentanones - bis(oxazoline) ligand - strain releaseSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751386.
- Supporting Information
Publication History
Received: 27 September 2022
Accepted after revision: 21 October 2022
Article published online:
16 November 2022
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