Synthesis of benzimidazole-derived chiral cyclic phosphoric acid and its application in asymmetric induction process

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-05-03 DOI:10.1080/00397911.2025.2495140

Swapnil J. Wagh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Baludev D. Dadas (Formal analysis Investigation Writing – original draft Writing – review & editing) , Trupti S. Tawde (Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Sumaiya Shaikh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Anil V. Karnik (Conceptualization Investigation Methodology Project administration Supervision Visualization Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

Chiral-pool approach has been invoked in a three-step synthetic protocol for the synthesis of 9-membered Benzimidazole-derived organo-Phosphoric Acid (HEBEN-PA). The HEBEN-PA has two fused aryl rings incorporated in the structure to minimize conformational changes. The HEBEN-PA was successfully employed as a Chiral Bronsted acid catalyst for the enantiomerically enriched dihydroquinazolinone synthesis. Synthesis of dihydroquinazolinone occurred with good yields. Effect of solvent, temperature, and the substituents on the level of enantioselectivity have been examined.

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苯并咪唑类手性环磷酸的合成及其在不对称诱导中的应用

手性池法被用于合成9元苯并咪唑衍生有机磷酸（HEBEN-PA）的三步合成方案。HEBEN-PA在结构中有两个融合的芳基环，以尽量减少构象变化。并成功地将HEBEN-PA作为手性Bronsted酸催化剂用于对映体富集的二氢喹唑啉酮的合成。以较好的收率合成了二氢喹唑啉酮。考察了溶剂、温度和取代基对对映体选择性水平的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.