Tetrahedron

Addition of organocopper reagents to allylic acrylates—the preparation of γ, δ-unsaturated acids and subsequent functionalization to γ-lactones

M Eriksson, A Hjelmencrantz, M Nilsson, T Olsson

文献索引：Eriksson, Magnus; Hjelmencrantz, Anders; Nilsson, Martin; Olsson, Thomas Tetrahedron, 1995 , vol. 51, # 46 p. 12631 - 12644

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被引用次数: 34

摘要

Conjugate addition of monoorganocopper compounds with iodotrimethylsilane (TMSI) or lithium diorganocuprates, with or without halosilanes, to allylic acrylates give allylic silyl ketene acetals/ester enolates. These can undergo Claisen rearrangement to give diastereomeric mixtures of γ, δ-unsaturated acids after aqueous work-up. For organocuprates, the diastereomeric ratio is strongly affected by the halosilane. Either ...