Diastereoselective α‐Alkylation of β‐Hydroxycarboxylic Esters through Alkoxide Enolates: Diethyl (2S, 3R)‐( + )‐3‐Allyl‐2‐Hydroxysuccinate from Diethyl (S)‐( − )‐Malate

作者: Dieter Seebach , Johannes Aebi , Daniel Wasmuth

DOI: 10.1002/0471264180.OS063.12

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摘要: Diastereoselective α-alkylation of β-hydroxycarboxylic esters through alkoxide enolates: diethyl (2S, 3R)-( + )-3-allyl-2-hydroxysuccinate from (S)-( − )-malate reactant: 9.51 g (50 mmol) ( )-diethyl (S)-malate product: allylated product product: (2S,3R)-3-allyl-2-hydroxysuccinic acid Keywords: alkylation, C-alkylation; assay methods, for butyllithium, with diphenylacetic acid; diisopropylamine; lithium diisopropylamide (LDA), preparation of; tetrahydrofuran; ethyl bromoacetate, lachrymator; tetrahydrofuran, purification; apparatus, maintaining an inert atmosphere; thermometer, Pt

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