スギウラ マサハル   Sugiura Masaharu
  杉浦 正晴
   所属   崇城大学  薬学部 薬学科
   崇城大学大学院  薬学研究科 薬学専攻
   職種   教授
言語種別 英語
発行・発表の年月 2011/01
形態種別 原著論文
査読 査読有り
標題 Synthesis of γ-amino alcohols from aldehydes, enamines, and trichlorosilane using Lewis base catalysts
執筆形態 共著
掲載誌名 Tetrahedron
掲載区分国外
巻・号・頁 67,pp.531-539
著者・共著者 Takeru Kashiwagi, Shunsuke Kotani, Masaharu Sugiura, Makoto Nakajima
概要 The reaction of aldehydes, enamines, and trichlorosilane in the presence of a Lewis base catalyst, particularly N-methylpyrrolidinone and DMF, affords γ-amino alcohols with a high diastereoselectivity. The method consists of C-C bond formation between an aldehyde and an enamine, and a subsequent intramolecular reduction of the resulting iminium ion intermediate. In most cases, one diastereomer is exclusively generated, and we propose a transition state model for the intramolecular reduction of the iminium ion intermediate. Enamines, prepared beforehand from the corresponding ketone and amine, can be used in the reaction without purification. Furthermore, enantioselective catalysis using a chiral Lewis base catalyst is possible, although the enantioselectivity is modest. The current tandem method offers the first, concise synthetic method of γ-amino alcohols from aldehydes and enamines. Copyright © 2010 Published by Elsevier Ltd.
DOI 10.1016/j.tet.2010.10.075
ISSN 00404020
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