Stereodivergence in the Ireland–Claisen Rearrangement of α-Alkoxy Esters
Organic Letters(2018)
摘要
A systematic investigation into the Ireland–Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
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关键词
ireland–claisen rearrangement
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