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Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization


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タイトル: Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization
著者: Kurosaki, Yuji / Fukuda, Tsutomu / Iwao, Masatomo
発行日: 2005年 3月28日
出版者: Elsevier Ltd.
引用: Tetrahedron, 61(13), pp.3289-3303;2005
抄録: Lateral lithiation of (S)-4-isopropyl-2-(o-tolyl)oxazoline in diethyl ether followed by the reaction with aldehydes in the presence of TMEDA produced the addition products with stereoselectivities up to 84% de. Utilization of TMEDA as a ligand is essential for the good selectivity. Rationale for the stereoselectivity is proposed based on ab initio calculation of the lateral lithio species. The major (S,S)-products lactonized faster than the minor (S,R)-products to the corresponding 3,4-dihydroisocoumarins under acidic conditions. Thus,(3S)-3,4-dihydroisocoumarins were obtained in good optical purities up to 97% ee by sequential application of these matched stereoselective reactions.
URI: http://hdl.handle.net/10069/20110
ISSN: 00404020
DOI: 10.1016/j.tet.2005.01.103
権利: Copyright (c) 2005 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/10069/20110

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