Iodine(III)‐Catalyzed Rearrangements of Imides: A Versatile Route to α, α‐Dialkylated α‐Hydroxy Carboxylamides. Issue 4 (2nd December 2014)

• Record Type: Journal Article
• Authors: Ulmer, Anna; Stodulski, Maciej; Kohlhepp, Stefanie V.; Patzelt, Christoph; Pöthig, Alexander; Bettray, Wolfgang; Gulder, Tanja
• Is Part Of: Chemistry. Volume 21:Issue 4(2015)
• Page Start: 1444
• Page End: 1448
• Publication Date: 2014-12-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201405888
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A tertiary hydroxy group α to a carboxyl moiety comprises a key structural motif in many bioactive substances. With the herein presented metal‐free rearrangement of imides triggered by hypervalent λ³‐iodane, an easy and selective way to gain access to such a compound class, namely α, α‐disubstituted‐α‐hydroxy carboxylamides, was established. Their additional methylene bromide side chain constitutes a useful handle for rapid diversification, as demonstrated by a series of further functionalizations. Moreover, the in situ formation of an iodine(III) species under the reaction conditions was proven. Our findings clearly corroborate that hypervalent λ³‐benziodoxolones are involved in these organocatalytic reactions.</p> </abstract>