A Novel Method for the Stereoselective Formation of Trans Bicyclic Ketones by Way of Oxidative Radical Cyclization

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Abstract
The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

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