Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

TETRAHEDRON LETTERS

卷:57

Article

Takahashi, Toshihisa¹  Reddy, U. V. Subba¹  Kohari, Yoshihito¹  Seki, Chigusa¹  Furuyama, Taniyuki²  Kobayashi, Nagao³  Okuyama, Yuko⁴  Kwon, Eunsang⁵  Uwai, Koji¹  Tokiwa, Michio⁶  Takeshita, Mitsuhiro⁶  Nakano, Hiroto¹ 

[1] Muroran Inst Technol, Div Sustainable & Environm Engn, Grad Sch Engn, 27-1 Mizumoto, Muroran, Hokkaido 0508585, Japan

[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

[3] Shinshu Univ, Fac Text Sci & Technol, Ueda, Nagano 3868567, Japan

[4] Tohoku Med & Pharmaceut Univ, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan

[5] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

[6] Tokiwakai Grp, 62 Numajiri Tsuduri Chou, Iwaki, Fukushima 9738053, Japan

关键词: Primary beta-amino alcohol;    Diels-Alder reaction;    3-Hydroxy-2-pyridone;    Enantioselective organocatalysis;   

DOI  :  10.1016/j.tetlet.2016.11.030

来源: Elsevier

【 摘 要 】

The simple primary beta-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple beta-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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