Tandem Reaction of (5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1222-1229. Previous Articles Next Articles

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(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应

谭越河¹，汪朝阳*^,1，郝志峰²，李建晓¹

(¹华南师范大学化学与环境学院广州 510006)
(²广东工业大学轻工化工学院广州 510006)

收稿日期:2011-01-26 修回日期:2011-03-06 发布日期:2011-03-21
通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com

Tandem Reaction of (5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids

Tan Yuehe¹ Wang Zhaoyang*^,1 Hao Zhifeng² Li Jianxiao¹

(¹School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
(²Faculty of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006)

Received:2011-01-26 Revised:2011-03-06 Published:2011-03-21
Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

Different kinds of amino acids, directly serving as nucleophiles, were reacted with (5S)-5-alkoxy-3,4-dihalo-5H-furan-2-ones via tandem asymmetric Michael addi-tion-elimination in the presence of potassium hydroxide to give 15 new optically active 5H-furan-2-one derivatives. The chemical structures and absolute configurations of these compounds were confirmed via rotation, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS, elemental analysis and X-ray single crystal diffraction.

Key words: (5S)-5-alkoxy-3,4-dihalo-5H-furan-2-one, amino acid, tandem Michael addi-tion-elimination, optical activity, multiple chiral center

Cite this article

TAN Yue-He, WANG Chao-Yang, HAO Zhi-Feng, LI Jian-Xiao. Tandem Reaction of (5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids[J]. Chin. J. Org. Chem., 2011, 31(08): 1222-1229.

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(5S)-5-烷氧基-3,4-二卤-2(5H)-呋喃酮与氨基酸的串联反应

Tandem Reaction of (5S)-5-Alkoxy-3,4-dihalo-5H-furan-2-ones with Amino Acids

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