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 2.9 3区化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-10-22 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。

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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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