The direct carbonylation of alkanes with CO suffers from low conversion owing to equilibrium constraints. Now, a strategy is presented that combines reversible alkane carbonylation with an asymmetric transformation to overcome the equilibrium limitations, enabling the synthesis of chiral β- and α-amino ketones from alkanes, CO and anilines.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 digital issues and online access to articles
$119.00 per year
only $9.92 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Peng, J.-B., Geng, H.-Q. & Wu, X.-F. The chemistry of CO: carbonylation. Chem 5, 526–552 (2019). A review article that presents the chemistry of carbonylation with CO.
Boese, W. T. & Goldman, A. S. Alkane carbonylation photocatalyzed by aromatic ketones under high CO pressure. Tetrahedron Lett. 33, 2119–2122 (1992). This paper reports alkane carbonylation photocatalysed by aromatic ketones.
Boese, W. T. & Goldman, A. S. Photochemical cyclohexane carbonylation cocatalyzed by d8 transition metal carbonyls and aromatic ketones and aldehydes. J. Am. Chem. Soc. 114, 350–351 (1992). This paper reports cyclohexane carbonylation photocatalysed by the combination of transition metals and ketones.
Jaynes, B. S. & Hill, C. L. Radical carbonylation of alkanes via polyoxotungstate photocatalysis. J. Am. Chem. Soc. 117, 4704–4705 (1995). This paper reports the carbonylation of alkanes through polyoxotungstate photocatalysis.
Ravelli, D., Fagnoni, M., Fukuyama, T., Nishikawa, T. & Ryu, I. Site-selective C–H functionalization by decatungstate anion photocatalysis: synergistic control by polar and steric effects expands the reaction scope. ACS Catal. 8, 701–713 (2018). A review article that provides an overview of decatungstate anion photocatalysis.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This is a summary of: Ding, W.-W. et al. Enantioselective synthesis of β- and α-amino ketones through reversible alkane carbonylation. Nat. Synth. https://doi.org/10.1038/s44160-023-00476-3 (2024).
Rights and permissions
About this article
Cite this article
Enantioselective assembly of β- and α-amino ketones from alkanes, CO and anilines. Nat. Synth 3, 432–433 (2024). https://doi.org/10.1038/s44160-023-00481-6
Published:
Issue Date:
DOI: https://doi.org/10.1038/s44160-023-00481-6