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Synthesis of enantiomerically enriched benzimidazole-triazoles: Application as organocatalyst for asymmertric Diels-Alder reaction
Indian Journal of Chemistry, Section B Pub Date : 2020-01-14
Jai V Sapre, Vaibhav N Khose, Trupti S Tawde, Swapnil J Wagh, Anil V Karnik

4-(Benzimidazolylmethyl)-1,2,3-triazole derivatives 8a-g and 9a-g have been developed using click chemistry protocol in regioselective manner and in high yields. These compounds have geometry to behave as chiral tweezers due to the presence of flexibly bound pi-rich hetero-aryl rings in addition to a chiral center. The synthesized chiral benzimidazole-triazoles have been found to be useful as organocatalysts for the enantioselective Diels-Alder (DA) reaction between anthrone 10 and maleimide detivatives 11a-g. Enantioselectivity levels have been found to be dependent on several factors including nature of substituents in benzimidazole-triazoles 8a-g and 9a-g.

中文翻译:

对映体富集的苯并咪唑-三唑的合成:作为有机催化剂用于不对称Diels-Alder反应

使用点击化学方案以区域选择性的方式并且以高收率开发了4-(苯并咪唑基甲基)-1,2,3-三唑衍生物8a-g9a-g。这些化合物由于手性中心以外还存在柔性结合的富含pi的杂芳基环,因此具有充当手性镊子的几何形状。已经发现合成的手性苯并咪唑-三唑可用作蒽酮10和马来酰亚胺衍生物11a-g之间的对映选择性Diels-Alder(DA)反应的有机催化剂。已经发现对映选择性水平取决于几个因素,包括苯并咪唑-三唑8a-g9a-g中取代基的性质。
更新日期:2020-01-14
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