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Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline

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タイトル: Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline
著者: Uchida, Katsuya / Fukuda, Tsutomu / Iwao, Masatomo
発行日: 2007年 7月23日
出版者: Elsevier Ltd.
引用: Tetrahedron, 63(30), pp.7178-7186;2007
抄録: Reaction of the laterally lithiated (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline with p-tolualdehyde gave an inseparable mixture of the addition products in low diastereoselectivity. However, the (S,S)-product cyclized to the corresponding 3,4-dihydroisocoumarin faster than the (S,R)-product on silica gel, which allowed to be produced both enantiomers of 8-methoxy-3-(p-tolyl)-3,4-dihydroisocoumarin in moderate to good optical purity [S-enantiomer: 75% ee; R-enantiomer: 96% ee]. This procedure was applied to the short-step synthesis of optically active 3,4-dihydroisocoumarin natural products such as (R)-8-hydroxy-3-(1-tridecyl)-3,4-dihydroisocoumarin and (R)-phyllodulcin.
キーワード: Asymmetric synthesis / 3,4-Dihydroisocoumarin / oxazoline / Lateral lithiation / Diastereomer-selective lactonization / Silica gel
URI: http://hdl.handle.net/10069/20106
ISSN: 00404020
DOI: 10.1016/j.tet.2007.04.092
権利: Copyright (c) 2007 Elsevier Ltd All rights reserved.
資料タイプ: Journal Article
原稿種類: author
出現コレクション:060 学術雑誌論文

引用URI : http://hdl.handle.net/10069/20106



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