Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Aryl Ketones Involving Free Phenolic Hydroxyl Group(s).

IF 3.9 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2024-09-23 DOI:10.1002/chem.202403055

Kedi Chang, Ruilong Chou, Pinke Yu, Linhong Zuo, Qixing Liu, Xumu Zhang, Congcong Yin, Haifeng Zhou

引用次数: 0

Abstract

A straightforward asymmetric transfer hydrogenation for accessing enantiomerically enriched secondary benzyl alcohols involving free phenolic hydroxyl group(s) under mild conditions was developed. Various of optical pure aryl alcohols with a remarkable functional group compatibility were achieved with 78 %-97 % yields, 84 %->99 % ee's and up to 10 000 TON. This rhodium-catalyzed reaction could be performed in a gram-scale without loss of the efficiency. Furthermore, the synthetic utility has also been demonstrated in the asymmetric synthesis of (S)-adrenaline and (S)-phenylephrine.

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铑催化的涉及游离酚羟基的芳基酮不对称转移加氢反应。

本研究开发了一种在温和条件下直接进行不对称转移加氢反应的方法，以获得含有游离酚羟基的对映体丰富的仲苄基醇。该反应生成了各种光学纯芳基醇，具有显著的官能团兼容性，产率为 78%-97%，ee 为 84%->99%，吨位高达 10 000 吨。这种铑催化反应可以在克级规模上进行，且不会降低效率。此外，该合成方法在 (S)- 肾上腺素和 (S)- 苯肾上腺素的不对称合成中也得到了证实。

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

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

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