Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

TETRAHEDRON

卷:72

Article

Yajima, Saki¹  Saitoh, Tsuyoshi^1,2,4  Kawa, Kohei¹  Nakamura, Kensuke³  Nagase, Hiroshi²  Einaga, Yasuaki^1,4  Nishiyama, Shigeru^1,4 

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Hiyoshi 3-14-1, Yokohama, Kanagawa 2238522, Japan

[2] Univ Tsukuba, Int Inst Integrat Sleep Med, Tennodai 1-1-1, Tsukuba, Ibaraki 3058575, Japan

[3] Maebashi Inst Technol, Dept Life Sci & Informat, Kamisadori 460-1, Maebashi, Gunma 3710816, Japan

[4] JST CREST ACCEL, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

关键词: Cyclohexadienone;    Diastereoselective hydrogenation;    Hypervalent iodobenzene;    Anodic oxidation;    Boron-doped diamond electrodes;   

DOI  :  10.1016/j.tet.2016.10.068

来源: Elsevier

【 摘 要 】

Cyclohexadienone derivatives possessing alpha-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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