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Iodine(III)‐Catalyzed Rearrangements of Imides: A Versatile Route to α,α‐Dialkylated α‐Hydroxy Carboxylamides
Author(s) -
Ulmer Anna,
Stodulski Maciej,
Kohlhepp Stefanie V.,
Patzelt Christoph,
Pöthig Alexander,
Bettray Wolfgang,
Gulder Tanja
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405888
Subject(s) - hypervalent molecule , moiety , chemistry , iodine , methylene , combinatorial chemistry , catalysis , bromide , stereochemistry , organic chemistry
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.