Cart
Communication
Catalytic Enantioselective Peroxidation of α,β-Unsaturated Ketones
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available α,β-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 17 ACS Journal articles (5 most recent appear below).
An Organocascade Kinetic Resolution
Patrick G. McGarraugh and Stacey E. Brenner-MoyerOrganic Letters2011 13 (24), 6460-6463An Organocascade Kinetic Resolution
Patrick G. McGarraugh and Stacey E. Brenner-MoyerOrganic Letters2011 13 (24), 6460-6463Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic ...
Chiral Counteranion Synergistic Organocatalysis under High Temperature: Efficient Construction of Optically Pure Spiro[cyclohexanone-oxindole] Backbone
Yu-Bao Lan, Hua Zhao, Zhao-Min Liu, Guo-Gui Liu, Jing-Chao Tao, and Xing-Wang WangOrganic Letters2011 Article ASAPChiral Counteranion Synergistic Organocatalysis under High Temperature: Efficient Construction of Optically Pure Spiro[cyclohexanone-oxindole] Backbone
Yu-Bao Lan, Hua Zhao, Zhao-Min Liu, Guo-Gui Liu, Jing-Chao Tao, and Xing-Wang WangOrganic Letters2011 Article ASAPThe combination of a cinchona-based chiral primary amine and a BINOL-phosphoric acid has been demonstrated as a powerful and synergistic catalyst system for the double Michael addition of isatylidene malononitriles with α,β-unsaturated ketones, to provide ...
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-...
Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides
Weiping Liu, Yuanming Li, Kaisheng Liu, and Zhiping LiJournal of the American Chemical Society2011 Article ASAPIron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides
Weiping Liu, Yuanming Li, Kaisheng Liu, and Zhiping LiJournal of the American Chemical Society2011 Article ASAPA three-component reaction of alkenes, aldehydes, and hydroperoxides catalyzed by FeCl2 to β-peroxy ketones has been achieved. This three-component reaction can be also applied to the synthesis of α-carbonyl epoxides, through either a stepwise base-...
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 ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue July 02, 2008
- Article ASAPJune 05, 2008
- Received: April 23, 2008
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
