N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Macrolactonization to Access Planar-Chiral Macrocycles

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-01-31 DOI:10.1021/acs.orglett.3c04200

Jiaming Wang, Meng Wang, Yilu Wen, Peng Teng, Chenyang Li* and Changgui Zhao*,

引用次数: 0

Abstract

An N-heterocyclic carbene (NHC)-catalyzed atroposelective macrolactonization has been disclosed. This approach affords planar-chiral macrocycles in high yields with excellent enantioselectivities over a broad substrate scope. Controlled experiments suggest that the enantioselectivity might arise from the cation–n interaction between the acyl azolium and the electron-rich moiety in the substrate. This mechanism is supported by density functional theory calculations, which also suggest an important π–π interaction in stabilizing the transition state.

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N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Macrolactonization to Access Planar-Chiral Macrocycles.

本研究公开了一种由 N-杂环碳烯（NHC）催化的异丙选择性大内酯化反应。这种方法可以在广泛的底物范围内以高产率和优异的对映选择性生成平面手性大环。受控实验表明，对映体选择性可能源于酰基偶氮鎓与底物中富电子分子之间的阳离子-n 相互作用。这一机制得到了密度泛函理论计算的支持，计算结果还表明，π-π 相互作用在稳定过渡态方面起着重要作用。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.