期刊
TETRAHEDRON
卷 65, 期 1, 页码 240-246出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.058
关键词
beta-Aroylacrylates; Sulfur ylide; Cyclopropane; Amidation; Microwave irradiation; Constrained scaffolds; DFT analysis; gamma-Turn mimics
Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl beta-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable gamma-turn mimic scaffolds. (C) 2008 Elsevier Ltd. All rights reserved.
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