Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet-Spengler Reaction for Concise Synthesis of CF₃-Substituted Tetrahydro-β-Carbolines.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-03 DOI:10.1021/acs.orglett.5c01864

Shigenobu Umemiya, Shinnosuke Nara, Masahiro Terada

引用次数: 0

Abstract

Fluorine-containing compounds are widely found in pharmaceuticals, agrochemicals, and functional materials. In particular, compounds containing enantioenriched trifluoromethyl groups are essential because they show metabolic stability, lipophilicity, and membrane permeability in vivo. In this study, an enantioselective Pictet-Spengler reaction of tryptamine derivatives with 1,1,1-trifluoro-4-[tris(1-methylethyl)silyl]-3-butyn-2-one catalyzed by a chiral phosphoric acid is demonstrated, which provides CF₃-containing chiral tetrahydro-β-carboline derivatives in good yields with high enantioselectivities.

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手性磷酸催化Pictet-Spengler反应简明合成cf3取代的四氢β-羰基烃。

含氟化合物广泛存在于药品、农用化学品和功能材料中。特别是，含有对映体富集的三氟甲基的化合物是必不可少的，因为它们在体内表现出代谢稳定性、亲脂性和膜渗透性。本研究证实了在手性磷酸的催化下，色胺衍生物与1,1,1-三氟-4-[三（1-甲基乙基）硅基]-3-丁-2-酮的Pictet-Spengler对映选择性反应，得到了含cf3的手性四氢β-羰基衍生物，收率高，对映选择性高。

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.

Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet-Spengler Reaction for Concise Synthesis of CF3-Substituted Tetrahydro-β-Carbolines.

Abstract

Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet-Spengler Reaction for Concise Synthesis of CF₃-Substituted Tetrahydro-β-Carbolines.