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 2014/07
形態種別 原著論文
査読 査読有り
標題 A Hydrogen Bond Rationale for the Enantioselective β-Alkenylboration of Enones Catalyzed by O-Monoacyltartaric Acids.
執筆形態 共著
掲載誌名 J. Org. Chem.
掲載区分国外
巻・号・頁 79,pp.6754-6758
著者・共著者 Grimblat, N.; Sugiura, M.; Pellegrinet, S. C.
概要 DFT calculations suggest that O-monoacyl l-tartaric acids catalyze the asymmetric conjugate alkenylboration of enones through transition structures that are stabilized by hydrogen-bonding interactions. Formation of a five-membered acyloxyborane is proposed. The hydrogen of the free carboxy group derived from the catalyst interacts with the carbonyl group of the cyclic acyloxyborane, stabilizing the transition structure and reducing the flexibility of the system. Additional stabilizing nonclassical CH···O hydrogen-bond interactions seem to determine the observed enantioselectivity. © 2014 American Chemical Society.
DOI 10.1021/jo5012398
ISSN 00223263
PMID 25001404
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