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<p></p><p>A pyrrole-based achiral atropisomeric macrocycle was rationally designed. Density functional theory calculations predicted that it possesses atropisomeric rigidity comparable to common cyclophanes, while exhibiting enhanced nucleophilicity. This combination indicates broad application potential in planar chiral derivatization. Achiral macrocycle has been successfully synthesized, and nuclear magnetic resonance studies confirmed its atropisomeric nature. Furthermore, the planar chiral derivatization of achiral macrocycle with electrophiles has been investigated. Under the chiral phosphoric acid catalysis, this derivatization proceeded with moderate stereo-selectivity.</p>

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Rational design, synthesis, and catalytic enantioselective derivatization of an achiral ansa-macrocycle

  • 期刊论文

  • 发表日期：

    2026年5月13日

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  • Rui Wang

摘要

A pyrrole-based achiral atropisomeric macrocycle was rationally designed. Density functional theory calculations predicted that it possesses atropisomeric rigidity comparable to common cyclophanes, while exhibiting enhanced nucleophilicity. This combination indicates broad application potential in planar chiral derivatization. Achiral macrocycle has been successfully synthesized, and nuclear magnetic resonance studies confirmed its atropisomeric nature. Furthermore, the planar chiral derivatization of achiral macrocycle with electrophiles has been investigated. Under the chiral phosphoric acid catalysis, this derivatization proceeded with moderate stereo-selectivity.