Iodine(V) Reagents in Organic Synthesis. Part 3. New Routes to Heterocyclic Compounds via o-Iodoxybenzoic Acid-Mediated Cyclizations: Generality, Scope, and Mechanism
Journal of the American Chemical Society2002Vol. 124(10), pp. 2233–2244
Citations Over TimeTop 1% of 2002 papers
K. C. Nicolaou, Phil S. Baran, Yong‐Li Zhong, Sofía Barluenga, Kevin W. Hunt, Remo Kranich, Juan A. Vega
Abstract
The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of delta-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cyclization reaction, this article describes a number of mechanistic investigations suggesting a single electron transfer from the anilide functionality to IBX and implicating a radical-based mechanism for the reaction.
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