Catalytic epoxidation of enones mediated by zinc alkylperoxide/tert-BuOOH systems

Marcin Kubisiak , Karolina Zelga , Iwona Justyniak , Ewa Tratkiewicz , Tomasz Pietrzak , Abdul R. Keeri , Zbigniew Ochal , Larissa Hartenstein , Peter W. Roesky , Janusz Lewiński

Abstract

The epoxidation of enones by zinc alkylperoxides is a challenging task receiving considerable attention in contemporary research; however, until now no welldefined zinc alkylperoxide based systems have been described. Here, a new catalytic method of epoxidation of enones in the presence of zinc alkylperoxides supported by N,N-bidentate ligands and tert-butyl hydroperoxide is reported. A new dimeric zinc alkylperoxide complex supported by an aminotroponiminate ligand is also presented. The studied catalytic systems show high activity in the epoxidation of trans-chalcone, and in the case of a chiral catalyst with the (S,S)-N,N′-bis(1-phenylethyl)aminotroponiminate ligand a moderate enantioselectivity was achieved.
Author Marcin Kubisiak (FC / DCOC)
Marcin Kubisiak,,
- Department Of Catalysis And Organometallic Chemistry
, Karolina Zelga (FC / DCOC)
Karolina Zelga,,
- Department Of Catalysis And Organometallic Chemistry
, Iwona Justyniak - [Institute of Physical Chemistry of the Polish Academy of Sciences]
Iwona Justyniak,,
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, Ewa Tratkiewicz (FC / DCOC)
Ewa Tratkiewicz,,
- Department Of Catalysis And Organometallic Chemistry
, Tomasz Pietrzak (FC / DCOC)
Tomasz Pietrzak,,
- Department Of Catalysis And Organometallic Chemistry
, Abdul R. Keeri - [Warsaw University of Technology (PW)]
Abdul R. Keeri,,
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- Politechnika Warszawska
, Zbigniew Ochal (FC / IBC / DDTB)
Zbigniew Ochal,,
- Department Of Drug Technology And Biotechnology
, Larissa Hartenstein - [Karlsruhe Institute of Technology]
Larissa Hartenstein,,
-
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, Peter W. Roesky - [Karlsruhe Institute of Technology]
Peter W. Roesky,,
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, Janusz Lewiński (FC / DCOC)
Janusz Lewiński,,
- Department Of Catalysis And Organometallic Chemistry
Journal seriesOrganometallics, ISSN 0276-7333
Issue year2013
Vol32
No19
Pages5263-5265
Publication size in sheets0.3
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1021/om400830e
URL http://pubs.acs.org/doi/abs/10.1021/om400830e
Languageen angielski
File
organometallics_2013_32_5263.pdf 441.77 KB
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 40.0, 06-12-2019, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 06-12-2019, ArticleFromJournal
Publication indicators Scopus Citations = 21; WoS Citations = 21; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.983; WoS Impact Factor: 2013 = 4.253 (2) - 2013=3.817 (5)
Citation count*3 (2015-03-08)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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