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Elsevier, Tetrahedron, 31(62), p. 7459-7465, 2006

DOI: 10.1016/j.tet.2006.05.013

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

Journal article published in 2006 by Chen-Guo Feng, 阮源萍, 黄培强, Jie Chen, Jian-Liang Ye, Yuan-Ping Ruan, Xiao Zheng, Pei-Qiang Huang ORCID
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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.