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

被引：14

作者：

Takahashi, Toshihisa ^{[1
]}

Reddy, U. V. Subba ^{[1
]}

Kohari, Yoshihito ^{[1
]}

Seki, Chigusa ^{[1
]}

Furuyama, Taniyuki ^{[2
]}

Kobayashi, Nagao ^{[3
]}

Okuyama, Yuko ^{[4
]}

Kwon, Eunsang ^{[5
]}

Uwai, Koji ^{[1
]}

Tokiwa, Michio ^{[6
]}

Takeshita, Mitsuhiro ^{[6
]}

Nakano, Hiroto ^{[1
]}

机构：

[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

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 51期

基金：

日本科学技术振兴机构;

关键词：

Primary beta-amino alcohol; Diels-Alder reaction; 3-Hydroxy-2-pyridone; Enantioselective organocatalysis; GLYCOSIDASE INHIBITORS; ORGANOCATALYST; 1,2-DIHYDROPYRIDINES; INTERMEDIATE; ALDEHYDES;

D O I：

10.1016/j.tetlet.2016.11.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：5771 / 5776

页数：6

共 35 条

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