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 2005/06
形態種別 原著論文
査読 査読有り
標題 Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine
執筆形態 共著
掲載誌名 Canadian Journal of Chemistry
掲載区分国外
巻・号・頁 83,pp.937-942
著者・共著者 Masaharu Sugiura, Chieko Mori, Keiichi Hirano, Shu Kobayashi
概要 Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid. © 2005 NRC Canada.
DOI 10.1139/v05-096
ISSN 00084042
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