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Updated: Jan 19, 2026
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
α-Photooxygenation of chiral aldehydes with singlet oxygen
Dominika J Walaszek1, Magdalena Jawiczuk1,2, Jakub Durka1,3
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Abstract:
Organocatalytic α-oxygenation of chiral aldehydes with photochemically generated singlet oxygen allows synthesizing chiral 3-substituted 1,2-diols. Stereochemical results indicate that the reaction in the presence of diarylprolinol silyl ethers is highly diastereoselective and that the configuration of a newly created stereocenter at the α-position depends predominantly on the catalyst structure. The absolute configuration of chiral 1,2-diols has been unambiguously established based on electronic circular dichroism (ECD) and TD-DFT methods.
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