Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins: Identification of Catalytic Intermediates and the Stereoselectivity‐Determining Step by ESI‐MS1. Issue 48 (2nd October 2013)

• Record Type: Journal Article
• Authors: Bächle, Florian; Duschmalé, Jörg; Ebner, Christian; Pfaltz, Andreas; Wennemers, Helma
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 48(2013)
• Page Start: 12619
• Page End: 12623
• Publication Date: 2013-10-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201305338
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Looking back</bold>: The asymmetric organocatalytic 1, 4‐addition of aldehydes to nitroolefins was studied by ESI‐MS. Analysis of the back reaction starting from quasienantiomeric mass‐labeled 1, 4‐adducts (see scheme) provided conclusive evidence for an enamine rather than an enol mechanism, and allowed identification of the enantioselectivity‐determining step.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t7btgw1" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>