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 2002/07
形態種別 原著論文
査読 査読有り
標題 Stereoselective synthesis of both syn- and anti-N-tert-alkylamines using highly stereospecific crotylation of ketone-derived acylhydrazones with crotyltrichlorosilanes
執筆形態 共著
掲載誌名 Journal of Organic Chemistry
掲載区分国外
巻・号・頁 67,pp.5359-5364
著者・共著者 Chikako Ogawa, Masaharu Sugiura, Shu Kobayashi
概要 Crotyltrichlorosilanes reacted with ketone-derived N-benzoylhydrazones in DMF without any catalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leading to both syn- and anti-N′-tert-alkyl-N-benzoylhydrazines. Different reactivities between (Z)- and (E)-crotylsilanes in terms of yields and selectivities were observed. A kinetic study with both geometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely to proceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes an axial position. Both diastereomers of allylation products can be converted to the corresponding α,α-disubstituted homoallylic amines without epimerization.
DOI 10.1021/jo0258599
ISSN 00223263
PMID 12126428
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