α-Photooxygenation of chiral aldehydes with singlet oxygen.

Autor:	Walaszek DJ; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland., Jawiczuk M; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.; Centre of New Technologies, University of Warsaw, Banacha 2c, 02-097 Warsaw, Poland., Durka J; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.; Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland., Drapała O; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.; Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland., Gryko D; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Jazyk:	angličtina
Zdroj:	Beilstein journal of organic chemistry [Beilstein J Org Chem] 2019 Aug 30; Vol. 15, pp. 2076-2084. Date of Electronic Publication: 2019 Aug 30 (Print Publication: 2019).
DOI:	10.3762/bjoc.15.205
Abstrakt:	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.
Databáze:	MEDLINE
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