Convenient Titanium(III)‐Catalyzed Synthesis of Cyclic Aminoketones and Pyrrolidinones—Development of a Formal [4+1] Cycloaddition1. Issue 28 (5th June 2013)

• Record Type: Journal Article
• Authors: Frey, Georg; Luu, Hieu‐Trinh; Bichovski, Plamen; Feurer, Markus; Streuff, Jan
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 28(2013)
• Page Start: 7131
• Page End: 7134
• Publication Date: 2013-06-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201302460
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Have it both ways</bold>: α‐Aminated ketones can be prepared by the titanium(III)‐catalyzed reductive radical cyclization of iminonitriles. Depending on the position of the nitrile at the imine carbon or nitrogen, cyclic aminoketones or pyrrolidin‐3‐ones with a tetrasubstituted α‐carbon can be formed in up to quantitative yield. In the latter case, the imine condensation and Ti^III catalysis correspond to a formal [4+1] cycloaddition.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg26mfwf8x" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>