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Syntheses of enantio-enriched chiral building blocks from L-glutamic acid

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Syntheses of enantio-enriched chiral building blocks from L-glutamic acid.htm (413bytes)
Date
2006-06
Author
Feng, Chen-Guo
Chen, Jie
Ye, Jian-Liang
Ruan, Yuan-Ping
阮源萍
Zheng, Xiao
Huang, Pei-Qiang
黄培强
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  • 化学化工-已发表论文 [14469]
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Abstract
Starting from lactone-amide 8, easily derived from L-glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-one (3) are reported. The building block 3 was converted to (2S,3R)-3-hydroxypipecolamide (6) by a three-step procedure. A solvent altered H-bonding capacity leading to a highly chemoselective tosylation of the primary hydroxyl group in the presence of an alpha-hydroxy-carboxamide was observed. (c) 2006 Elsevier Ltd. All rights reserved.
Citation
TETRAHEDRON,2006,62(31):7459-7465
URI
http://dx.doi.org/doi:10.1016/j.tet.2006.05.013
https://dspace.xmu.edu.cn/handle/2288/10358

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