title: Iodine(III)-catalyzed rearrangements of imides: a versatile route to α,α-dialkylated α-hydroxy carboxylamides.
abstract: 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 λ(3)-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 λ(3)-benziodoxolones are involved in these organocatalytic reactions.
authors.affiliation: Department Chemie and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany) http://www.halogene.ch.tum.de.
authors.forename: Anna
authors.initials: A
authors.lastname: Ulmer
authors.forename: Maciej
authors.initials: M
authors.lastname: Stodulski
authors.forename: Stefanie V
authors.initials: SV
authors.lastname: Kohlhepp
authors.forename: Christoph
authors.initials: C
authors.lastname: Patzelt
authors.forename: Alexander
authors.initials: A
authors.lastname: Pöthig
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Bettray
authors.forename: Tanja
authors.initials: T
authors.lastname: Gulder
keywords: hypervalent compounds; imides; iodine; rearrangements; α-hydroxy carboxylamides