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

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-10-16 Epub Date: 2024-10-14 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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Abstract

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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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。
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。
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来源期刊
Organic & Biomolecular Chemistry
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.
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