Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (12): 1890-1897. Previous Articles Next Articles

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无保护α-氨基酸合成多手性中心2(5H)-呋喃酮化合物

宋秀美¹^{,2，谭越河¹，李建晓¹，汪朝阳*^,1}

(¹华南师范大学化学与环境学院广州 510006)
(²湛江师范学院化学科学与技术学院化学与材料研究中心
广东高校新材料工程技术开发中心湛江 524048)

收稿日期:2010-05-26 修回日期:2010-07-06 发布日期:2010-07-23
通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com

Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids

Song Xiumei¹^{,2 Tan Yuehe¹ Li Ji-anxiao¹ Wang Zhaoyang*^,1}

(¹ School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
(² Research Center of Chemistry and Marterials, Development Center for New Ma-terials Engineering & Technology in Universities of Guangdong, Chemistry Science and Technology School, Zhanjiang Normal College, Zhanjiang 524048)

Received:2010-05-26 Revised:2010-07-06 Published:2010-07-23
Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com

Abstract

Five unprotected α-amino acids, serving as nucleophiles, were reacted with different (5S)-5- alkoxy-3,4-dihalo-5H-furan-2-ones via tandem Michael addition-elimination to give 15 new optically active 5H-furan-2-one derivatives. The chemical structures and absolute configurations of these compounds with multiple chiral centers 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, unprotected α-amino acid, tandem Michael addition-elimination, optical activity, multiple chiral center

Cite this article

SONG Xiu-Mei, TAN Yue-He, LI Jian-Xiao, WANG Chao-Yang. Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids[J]. Chin. J. Org. Chem., 2010, 30(12): 1890-1897.

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无保护α-氨基酸合成多手性中心2(5H)-呋喃酮化合物

Synthesis of 5H-Funan-2-ones with Multiple Chiral Centers Directly from Unprotected α-Amino Acids

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