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 2001/10
形態種別 原著論文
査読 査読有り
標題 Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones
執筆形態 共著
掲載誌名 Journal of the American Chemical Society
掲載区分国外
巻・号・頁 123,pp.9493-9499
著者・共著者 R. Hirabayashi, C. Ogawa, M. Sugiura, S. Kobayashi
概要 Allyltrichlorosilanes reacted with benzoylhydrazones in DMF without the use of any catalyst to afford the corresponding homoallylic benzoylhydrazines in good to high yields. The reactions proceeded at 0°C to room temperature under mild conditions. In addition, it was found that the reactions tolerated well the steric hindrance of hydrazones and allyltrichlorosilanes. Indeed, ketone-derived benzoylhydrazones reacted with allyltrichlorosilane smoothly to afford the corresponding N′-tert-alkyl-N-benzoylhydrazines in high yields. In crotylation with (E)- and (Z)-crotyltrichlorosilanes, syn- and anti-adducts were stereospecifically obtained, respectively. These reactions are most likely to proceed via a cyclic chairlike transition state where the R group takes an axial position. When α-heteroatom-substituted chiral benzoylhydrazones were used, high anti-diastereoselectivities were observed. These adducts can be readily converted to homoallylic amines in high yields without epimerization.
DOI 10.1021/ja011125m
ISSN 00027863
PMID 11572669
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