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Synthesis 2024; 56(08): 1285-1296
DOI: 10.1055/a-2232-8776
DOI: 10.1055/a-2232-8776
paper
DBU-Mediated Oxidation of β-Dicarbonyls: Formation of Hydroxylated and Rearranged Products under Air Atmosphere
Financial support from the National Natural Science Foundation of China (No. 32130083).
Abstract
The oxidation of different β-dicarbonyls in acetonitrile has been explored under an air atmosphere in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The presence of DBU resulted in the formation of hydroxylated products or rearrangement products derived from hydroxylated products. Specifically, the transformation of 2-oxocyclopentanecarboxylates to 2-hydroxyhexanedioates was achieved with good yields when additional 1,2-bis(diphenylphosphino)ethane and ROH were present. DBU proved to be indispensable for this transformation and showed specificity beyond its usual role as a base.
Key words
β-diketones - β-keto esters - β-keto amides - 1,8-diazabicyclo[5.4.0]undec-7-ene - α-hydroxylation - rearrangementSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2232-8776.
- Supporting Information
Publication History
Received: 24 November 2023
Accepted after revision: 19 December 2023
Accepted Manuscript online:
19 December 2023
Article published online:
24 January 2024
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