Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst

Title
Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst
Publication Date
2023-08-18
Author(s)
Legendre, Sarah V A M
Sumby, Christopher J
Karton, Amir
( author )
OrcID: https://orcid.org/0000-0002-7981-508X
Email: akarton@une.edu.au
UNE Id une-id:akarton
Greatrex, Ben W
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
American Chemical Society
Place of publication
United States of America
DOI
10.1021/acs.joc.3c00278
UNE publication id
une:1959.11/58468
Abstract

Bifunctional thiourea/amine organocatalysts have been used for the desymmetrization of meso-endoperoxides using the Kornblum−DeLaMare reaction, giving 4-hydroxyketones in 78−98% yields with ≤98:2 enantioselectivity. The influence of the catalyst structure, solvent, and temperature was examined. The most promising catalyst was applied to the kinetic resolution of racemic endoperoxides to give enantioenriched materials (≤99:1 er).
Link
link
Citation
The Journal of Organic Chemistry, v.88, p. 11444-11449
ISSN
1520-6904
0022-3263
Start page
11444
End page
11449

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