手性磷酸促成肉桂醛衍生的 N-芳基硝基与 2-吲哚甲醇的不对称 [3 + 3] 环加成。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-10-16 DOI:10.1039/d4ob01365d

Ning Zou , Yu-Zheng Wu , Zi-Wei Shang , Yu-Wei Cao , Li-Min Liao , Cui Wei , Dong-Liang Mo , Wen-Jun Zhou

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引用次数: 0

摘要

我们介绍了一种手性磷酸（CPA）催化的肉桂醛衍生 N-芳基硝基与 2-吲哚甲醇的不对称 [3 + 3] 环加成反应，从而制备出各种吲哚融合的 1,2-噁嗪类化合物，产率高（高达 96%），对映选择性极佳（>99% ee）。对照实验表明，氢键在控制产物的对映体选择性方面发挥了重要作用。该策略为从 N-芳基硝基与 2-吲哚甲醇构建对映体丰富的吲哚融合 1,2-oxazines 提供了一条有效途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid†

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Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid†

We described a chiral phosphoric acid (CPA) catalyzed asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolylmethanols to prepare various indole-fused 1,2-oxazines in high yields (up to 96%) with excellent enantioselectivity (>99% ee). Control experiments indicate that hydrogen bonding plays important roles in controlling the enantioselectivity of products. This strategy provides an efficient pathway to construct enantioenriched indole-fused 1,2-oxazines from N-aryl nitrones with 2-indolylmethanols.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.