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On the Phenyliodine(III)‐Bis(trifluoroacetate)‐Mediated Olefin Amidohydroxylation Reaction
Author(s) -
Tellitu Imanol,
Urrejola Andrea,
Serna Sonia,
Moreno Isabel,
Herrero M. Teresa,
Domínguez Esther,
SanMartin Raul,
Correa Arkaitz
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600782
Subject(s) - chemistry , piperidine , moiety , olefin fiber , pyrrolidine , nucleophile , intramolecular force , molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis
When appropriately substituted amides are treated with PIFA in a non‐nucleophilic solvent like trifluoroethanol, a stable N ‐acylnitrenium ion is generated. If under such conditions a C=C double bond is present in the molecule, an intramolecular cyclization process takes place in an exo mode with additional generation of a hydroxy group at the terminal position of the original olefin moiety to render a series of pyrrolidine and piperidine derivatives. In this paper, proofs are offered to conclude that, according to our assumption, an ionic mechanism rather than a radical one must be considered. Additionally, a study of the scope of this cyclization protocol is conducted using substrates with different substituents either on the amidic nitrogen or all along the carbon chain.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)