Facial selectivity in the addition of lithium dimethylcuprate to 6-substituted tricyclo 5.2.1.0(2,6) deca-4,8-dienones. Synthesis of beta-substituted cyclopentenones using flash vacuum thermolysis
摘要：
The stereoselectivity of the nucleophilic addition of lithium dimethylcuprate and lithium di-n-pentylcuprate to 6-substituted tricyclo[5.2.1.0(2,6)]deca-4,8-dienones was investigated. It was shown that substituents at the 6-position can either exert a steric effect or an electronic effect. Steric approach control predominantly giving the endo product was observed for 6-alkyl substituents. Stereoelectronic control could be adequately rationalised using the Cieplak model. Flash vacuum thermolysis was used to prepare a series of -substituted cyclopentenoids. The sequence leading to cyclopentenoids has an attractive scope.
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关键词：
sequential one pot reaction beta-cyclodextrin water as a solvent supramolecular catalysis recyclability of catalyst
DOI：
10.1071/CH14094
被引量：
年份：
2014
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