Stereospecific Substitution of Enantiomerically Pure 1-(2-Pyridinyl)ethyl Methanesulfonate with β-Dicarbony Compounds

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概要

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• The alkylation of the sodium salt of the malonic acid diester with (R)-1-(2-pyridinyl)ethyl methanesulfonate (2) gave the dimethyl (R)-[1-(2-pyridinyl)ethyl]maloaate (3a), stereospecifically. The alkylation reaction of methyl acetoacetate gave the methyl (2'S,2R/2S)-3-oxo-2-[1-(2-pyridinyl)ethyl]butanoate (3d) along with the methyl (S)-3-[1-(2-pyridinyl)ethoxy]-2-butenoate (4d). The acid hydrolysis and decarboxylation of 3d under acidic conditions gave (R)-4-(2-pyridinyl)pentan-2-one (6), and the alkylation of methyl (R)-[1-(2-pyridinyl)ethyl]acetoacetate with benzyl bromide gave a mixture of C-benzylated and O-benzylated products 7 and 8.

• 公益社団法人日本薬学会の論文
• 2002-05-01

著者

• Hamada Masahiro

  Kyoto Pharmaceutical University

• UENISHI Junichi

  Kyoto Pharmaceutical University

関連論文

• Stereospecific Substitution of Enantiomerically Pure 1-(2-Pyridinyl)ethyl Methanesulfonate with β-Dicarbony Compounds
• Stereoselective Synthesis of C3-C12 Dihydropyran Portion of Antitumor Laulimalide Using Copper-Catalyzed Oxonium Ylide Formation-[2, 3] Shift

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