α-Photooxygenation of chiral aldehydes with singlet oxygen

Autor: Dominika J. Walaszek, Magdalena Jawiczuk, Jakub Durka, Olga Drapała, Dorota Gryko
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 2076-2084 (2019)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.205
Popis: 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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