Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy1. Issue 20 (9th April 2013)

• Record Type: Journal Article
• Authors: Hu, Pengfei; Hu, Jian; Jiao, Jiajun; Tong, Xiaofeng
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 20(2013)
• Page Start: 5319
• Page End: 5322
• Publication Date: 2013-04-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201300526
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Gone, without a trace</bold>: The in situ reaction of 2‐(acetoxymethyl)buta‐2, 3‐dienoate and a secondary amine produces a 2‐methylene‐3‐oxobutanoate equivalent that can be used in asymmetric [4+2] annulations with <italic>N</italic>‐tosylimines to provide tetrahydropyridines in good to excellent yields and enantioselectivities. The amine is easily recovered and acts as a traceless auxiliary.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1zsxhrtf" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>