Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst

Sarah V A M Legendre; Christopher J Sumby; Amir Karton; Ben W Greatrex

doi:10.1021/acs.joc.3c00278

Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst

Sarah V A M Legendre
, Christopher J Sumby
, Amir Karton
, Ben W Greatrex

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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).

Original language	English
Pages (from-to)	11444-11449
Journal	The Journal of Organic Chemistry
Volume	88
Early online date	8 Aug 2023
DOIs	https://doi.org/10.1021/acs.joc.3c00278
Publication status	Published - 18 Aug 2023

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https://hdl.handle.net/1959.11/58468

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title = "Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst",

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).",

author = "Legendre, \{Sarah V A M\} and Sumby, \{Christopher J\} and Amir Karton and Greatrex, \{Ben W\}",

year = "2023",

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doi = "10.1021/acs.joc.3c00278",

language = "English",

volume = "88",

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journal = "The Journal of Organic Chemistry",

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T1 - Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst

AU - Legendre, Sarah V A M

AU - Sumby, Christopher J

AU - Karton, Amir

AU - Greatrex, Ben W

PY - 2023/8/18

Y1 - 2023/8/18

N2 - 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).

AB - 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).

U2 - 10.1021/acs.joc.3c00278

DO - 10.1021/acs.joc.3c00278

M3 - Article

SN - 0022-3263

VL - 88

SP - 11444

EP - 11449

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

ER -

Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst

Abstract

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