α, β-エポキシ基により制御されたカルボニル化合物およびイミン類への求核試剤のジアステレオ選択的付加反応とその応用

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Diastereoselective addition of nucleophiles to carbonyl and imine compounds with α- and/or β-substituents has been a valuable tool in the synthesis of complex molecules. Since optically active epoxides are easily accessible by Sharpless asymmetric epoxidation, the utiltiy of this group as a stereocontrolling element in such reactions is getting more and more highlighted recently. This account surveys diastereoselectivities in the nucleophilic additions to the C = X bonds found in i) α, β-epoxy aldehydes, ii) α, β-epoxy ketones, iii) α, β-epoxy imines, and iv) γ, δ-epoxy-α, β-unsaturated carbonyl compounds (conjugate addition) in this order and also presents some devices to achieve high selectivities as well as possible rationale of the stereochemical outcome in certain cases. Application of these reactions to the synthesis of biologically active compounds is also illustrated.
社団法人有機合成化学協会の論文