キハラ ノブヒロ   Kihara Nobuhiro
  木原 伸浩
   所属   神奈川大学  理学部 化学科
   職種   教授
言語種別 英語
発行・発表の年月 2010
形態種別 学術雑誌
査読 査読あり
招待 招待あり
標題 Asymmetric Benzoin Condensation: Unique Asymmetric Field Constructed by the Cooperation of Rotaxane Compnents
執筆形態 共著
掲載誌名 Phosphorus, Sulfur, and Silicon
巻・号・頁 185(5-6),pp.1182-1205
著者・共著者 Yuya Tachibana, Nobuhiro Kihara, Kazuko Nakazono, Toshikazu Takat
概要 A binaphthyl group as the chiral auxiliary was introduced in either the wheel or the axle component of the rotaxanes. Rate of the catalytic benzoin condensation of benzaldehyde with a rotaxane catalyst without the binaphthyl moiety was compared with its axle component to understand the effect of wheel component. Among several solvents used, methanol was the best solvent, which showed the highest yield (98%) of benzoin in the presence of 5 mol% of either the rotaxane and the axle catalysts. The benzoin condensations of aromatic aldehydes catalyzed by the chiral rotaxanes gave optically active benzoins with 0-32% e.e. in 5-92% yield. From the results, two intrarotaxane chirality transfers are confirmed: (i) through-space chirality transfer from wheel to axle and (ii) through-bond chirality transfer controlled with an achiral wheel. The importance and possibility of the orotaxane fieldo as a particular reaction field are demonstrated.
DOI 10.1080/10426501003773589
ISSN 1042-6507