Copper‐Catalyzed Three‐Component Annulations of Alkenes, Nitrosoarenes, and N‐Hydroxyallylamines To Form Fused Oxazinane/Isoxazolidine Heterocycles

Abstract

One-pot cascade annulations among nitrosoarenes, alkenes,a nd N-hydroxyallylamines have been achieved with CuCl/O 2 catalysts,f orming fused oxazinane/isoxazolidine heterocycles with excellent diastereoselectivity (d.r. > 20:1). To enhance the synthetic utility,w ed eveloped as uccessive cleavage of the two N À Obonds of the resulting heterocycles.A mechanism involving dipolar [3+ +2] cycloadditions of nitrone intermediates with their tethered alkenes is postulated for formation of these heterocycles.Supportinginformation for this article can be found under: http://dx.Scheme 1. Single and double cleavages of NÀObonds. Scheme 2. Control experiments.Scheme 3. Apostulated mechanism for three-component annulations. Angewandte ChemieCommunications

Synthesis of Hydroxysuccinimide Substituted Indolin-3-ones via One-Pot Cascade Reaction of o-Alkynylnitrobenzenes with Maleimides under Au(III)–Cu(II) Relay/Synergetic Catalysis

“…On the basis of experimental results and related pioneering studies by Greci,11a,b Yamamoto,11c and Ramana,11d,e,6f 12 In the current reaction, on the other hand, this transformation was accomplished under neutral conditions without using any strong reducing reagents. This should be considered as an advantageous feature of this method since it allows this method to be used for substrates bearing functional groups susceptible to strong reductive conditions.…”

Photo-induced redox cascade reaction of nitroarenes and amines

“…This skeleton is a key substructure of many bioactive compounds, and constitutes a versatile platform for further chemical transformations. [35][36][37][38][39][40][41][42] The previous synthetic route [43][44][45][46] to this structural unit involves the utilization of unstable and perishable aldehydes and hydroxylamine, resulting in a limited substrate scope. For example, only the electron-withdrawing groups, such as Boc-and Cbz-protected hydroxylamines, are tolerated in these reactions.…”