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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes
Batoul Rkein1, Romain Coffinier1, Marian Powderly1
1Normandie Université, UNIROUEN, CNRS, INSA Rouen, COBRA laboratory, F-76000 Rouen, France. isabelle.chataigner@univ-rouen.fr.
Abstract:
Simple nitroarenes such as nitronaphthalenes and nitroquinolines smoothly undergo dearomatizing [4+2] cycloadditions with silyloxydienes under 16 kbar. Highly functionalized 3-dimensional polycyclic adducts bearing a tetrasubstituted carbon centre at the ring junction are obtained in one step from simple raw materials. This unprecedented dearomative Diels-Alder process is performed at room temperature without any chemical promoter, illustrating the exceptional role of high pressure as a physical promoter.
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