Husain Ali A, Maknenko Arthur M, Bisht Kirpal S
Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida, 33620, USA.
Chemistry. 2016 Apr 25;22(18):6223-7. doi: 10.1002/chem.201600352. Epub 2016 Mar 21.
The synthesis of novel spatially directional multivalent resorcin[4]arene cavitand glycoconjugates (RCGs) and their ability to catalyze organic reactions is reported. The β-d-glucopyranoside moieties on the upper rim of the "bowl"-shaped resorcin[4]arene cavitand core are capable of multiple hydrogen-bond interactions resulting in a pseudo-cavity, which has been investigated for organic transformations in aqueous media. The RCGs have been demonstrated to catalyze thiazole formation, thiocyanation, copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), and Mannich reactions; they impart stereoselectivity in the three-component Mannich reaction. Thermodynamic values obtained from (1) H diffusion-ordered spectroscopy (DOSY) experiments suggest that the upper saccharide cavity of the RCG and not the resorcin[4]arene cavity is the site of the complexation event.
报道了新型空间定向多价间苯二酚[4]芳烃穴状配体糖缀合物（RCG）的合成及其催化有机反应的能力。“碗”状间苯二酚[4]芳烃穴状配体核心上缘的β-D-吡喃葡萄糖苷部分能够进行多种氢键相互作用，从而形成一个假腔，已对其在水介质中的有机转化进行了研究。已证明RCG可催化噻唑形成、硫氰化、铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）和曼尼希反应；它们在三组分曼尼希反应中具有立体选择性。从（1）H扩散排序光谱（DOSY）实验获得的热力学值表明，RCG的上糖腔而非间苯二酚[4]芳烃腔是络合事件发生的位点。
