Asymmetric Intramolecular Oxa‐Michael Reactions of Cyclohexadienones Catalyzed by a Primary Amine Salt1. Issue 6 (20th December 2012)

• Record Type: Journal Article
• Authors: Wu, Wenbin; Li, Xin; Huang, Huicai; Yuan, Xiaoqian; Lu, Junzhu; Zhu, Kailong; Ye, Jinxing
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 6(2013)
• Page Start: 1743
• Page End: 1747
• Publication Date: 2012-12-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201206977
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Michael brings the rings</bold>: An asymmetric intramolecular oxa‐Michael reaction involving iminium activation has been developed. This reaction provides enantioenriched 1, 4‐dioxane derivatives with up to 99 % yield and 98 % <italic>ee.</italic> The method allows for concise and stereoselective access to stereodiverse, complex tetracyclic compounds containing a bicyclo[2.2.2]octan‐2‐one backbone with multiple chiral centers.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1v48gh14" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>