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Abstract
This chapter describes the stereochemistry and asymmetric synthesis involving radical reactions. First, an introduction to radical chain mechanisms is provided. Different chain methods with various chain initiators are described throughout. Diastereoselective radical reactions involving cyclic and acyclic radicals are presented. Diastereoselective radical cyclizations are described in detail with mechanisms and synthetic applications in respect of hexenyl radical cyclizations, cis ring fusions, tandem radical cyclizations and cyclizations onto oximes and hydrazones. Samarium diiodide-mediated ketyl radical cyclizations are presented. Stereoselective dissolving metal reductions of alkynes and enones are included. Asymmetric radical reactions using chiral sultam and oxazolidinone auxiliaries, chiral Lewis acids based on bisoxazoline ligands and chiral Brønsted acids as ammonium salts of quinine or quinidine are described. Asymmetric organocatalysis based on a SOMO catalysis mechanism and a dual catalysis mechanism with a combination of photoredox catalysis and organocatalysis are described.
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