Stereoselective synthesis of 1,2,3-triazolyl-functionalized isoxazolidines, via two consecutive 1,3-dipolar cycloadditions, as precursors of unnatural amino acids

被引：11
作者：
Aouadi, Kaiss [1 ,2 ]
Vidal, Sebastien [1 ]
Msaddek, Moncef [2 ]
Praly, Jean-Pierre [1 ]
机构：
[1] Univ Lyon, Inst Chim & Biochim Mol & Supramol, UMR CNRS 5246, Lab Chim Organ Glycochim 2, F-69622 Villeurbanne, France
[2] Univ Monastir, Lab Synth Heterocycl, Fac Sci Monastir, Monastir 5000, Tunisia
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 15期
关键词：
Chiral nitrone; 1,3-Dipolar cycloaddition; Isoxazolidine; 1,2,3-Triazole; Click chemistry; TERMINAL ALKYNES; CHIRAL NITRONES; CLICK CHEMISTRY; GENETIC-CODE; ALKENES; DERIVATIVES; ACCESS; PROTEINS; AZIDES;
D O I：
10.1016/j.tetlet.2013.01.125
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of a (-)-menthone-derived nitrone to allyl bromide under microwave irradiation afforded, stereoselectively, the corresponding chiral isoxazolidine in 98% yield. After substitution of the bromine atom by an azide group (98% yield), another 1,3-cycloaddition with various alkynes led to a series of 1,2,3-triazolyl-functionalized isoxazolidines (similar to 85% yield). Removal of the chiral auxiliary under acid-catalysis appeared to be a limiting step toward 5-substituted isoxazolidines, which were isolated in modest yields. For a general and reliable access to 5-(triazolyl)methyl-substituted isoxazolidines, which are new compounds and valuable precursors of unnatural amino acids, performing the CuAAC cycloaddition as the final step is recommended. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：1967 / 1971
页数：5
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