Abstract
This chapter deals with stereochemistry and asymmetric approaches to photochemical reactions. Photochemical [2+2] cycloadditions are described with respect to stereospecificity of alkene cycloadditions and diastereoselectivity of enone cycloadditions with mechanisms and synthetic applications. Visible light photocatalysis of enone cycloadditions with photoredox catalyst is also discussed. The Paternò–Büchi reaction is presented with endo-/exo-selectivity and synthetic applications. The stereochemistry of electrocyclic reactions including photochromism and vitamin D synthesis is described. The classical photo-induced remote functionalization in steroid systems with the Hofmann–Löffler–Freytag reaction and the Barton reaction is included. The stereochemical aspects of cyclohexadienone rearrangement and di-π-methane rearrangement are also covered. Asymmetric photochemistry with respect to asymmetric photocycloadditions is presented using substrate control and chiral auxiliary control. Recent approaches to asymmetric photocatalysis using chiral Lewis acid photocatalyst and dual photoredox/chiral Lewis acid catalysis are described with mechanistic interpretations.
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