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Catalytic Asymmetric Epoxidation of Cyclic Enones
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Abstract

A highly enantioselective epoxidation of cyclic enones with hydrogen peroxide has been developed that is catalyzed by chiral primary amine salts.
Citing Articles
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This article has been cited by 22 ACS Journal articles (5 most recent appear below).

Theoretical Investigation on the Chiral Diamine-Catalyzed Epoxidation of Cyclic Enones: Mechanism and Effects of Cocatalyst
Ping-Li Lv, Rong-Xiu Zhu, Dong-Ju Zhang, Chong-Gang Duan, and Cheng-Bu LiuThe Journal of Physical Chemistry A2012 116 (4), 1251-1260Theoretical Investigation on the Chiral Diamine-Catalyzed Epoxidation of Cyclic Enones: Mechanism and Effects of Cocatalyst
Ping-Li Lv, Rong-Xiu Zhu, Dong-Ju Zhang, Chong-Gang Duan, and Cheng-Bu LiuThe Journal of Physical Chemistry A2012 116 (4), 1251-1260The asymmetric epoxidation of 2-cyclohexen-1-one with aqueous H2O2 as oxidant, 1,2-diaminocyclohexane as catalyst, and a Brønsted acid trifluoroacetic acid (TFA) as cocatalyst has been studied by performing density functional theory calculations. It is ...

Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters
Aijun Lin, Junying Wang, Haibin Mao, Huiming Ge, Renxiang Tan, Chengjian Zhu, and Yixiang ChengOrganic Letters2011 Article ASAPOrganocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters
Aijun Lin, Junying Wang, Haibin Mao, Huiming Ge, Renxiang Tan, Chengjian Zhu, and Yixiang ChengOrganic Letters2011 Article ASAPAn asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-...

Effect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers
Piotr Kwiatkowski, Krzysztof Dudziński, and Dawid ŁyżwaOrganic Letters2011 Article ASAPEffect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers
Piotr Kwiatkowski, Krzysztof Dudziński, and Dawid ŁyżwaOrganic Letters2011 Article ASAPThe significant effect of hydrostatic pressure on the difficult organocatalytic 1,4-conjugate addition of nitroalkanes to prochiral sterically congested β,β-disubstituted enones is demonstrated. This approach allows for the synthesis of γ-nitroketones ...

Iron-Catalyzed Asymmetric Epoxidation of β,β-Disubstituted Enones
YASUHIRO NISHIKAWA and Hisashi YamamotoJournal of the American Chemical Society 0 (ja),Iron-Catalyzed Asymmetric Epoxidation of β,β-Disubstituted Enones
YASUHIRO NISHIKAWA and Hisashi YamamotoJournal of the American Chemical Society 0 (ja),The combination of Fe(OTf)2 and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones which have been heretofore inaccessible substrate classes. The reactions provide highly enantioenriched α,β-...

Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
Piotr Kwiatkowski, Teresa D. Beeson, Jay C. Conrad, and David W. C. MacMillanJournal of the American Chemical Society2011 133 (6), 1738-1741Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
Piotr Kwiatkowski, Teresa D. Beeson, Jay C. Conrad, and David W. C. MacMillanJournal of the American Chemical Society2011 133 (6), 1738-1741The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new ...
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History
- Published In Issue May 14, 2008
- Article ASAPApril 19, 2008
- Received: February 17, 2008
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