Enantioselective Synthesis of Chiral 3-Substituted Tetrahydroquinolines via a Pd-Catalyzed C–C Cleavage/C–C Coupling Sequence

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI:10.1021/acs.orglett.6c03823

Cheng-Yu Li, Xiao-Jing Liu, Zhen-Ting Mao, Yi-Xia Jia, Ren-Xiao Liang

引用次数: 0

Abstract

A palladium-catalyzed asymmetric synthesis of 3-substituted tetrahydroquinolines (THQs) through a C–C cleavage/C–C coupling sequence has been developed. By employing Pd(OAc)₂/Josiphos L7 as the catalyst, an array of chiral tetrahydroquinolines bearing a C3-ketone pendant was afforded in good to excellent yields and enantioselectivities by using 3-(2-bromoaniline)-tethered cyclobutanols as substrates. Control experiments revealed that only cis-substrates were able to participate in the reaction. In addition, several synthetic transformations derived from the ketone moiety were carried out to demonstrate the practical utility of this protocol.

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对映选择性：通过pd催化C-C裂解/ c -偶联序列合成手性3-取代四氢喹啉

摘要研究了钯催化的C-C裂解/ C-C偶联不对称合成3-取代四氢喹啉（THQs）的方法。以Pd(OAc)2/Josiphos L7为催化剂，以3-（2-溴苯胺）系环丁醇为底物，制备了一系列具有3-酮链的手性四氢喹啉，并具有良好的产率和对映选择性。对照实验表明，只有顺式底物能够参与反应。此外，还进行了几个由酮段衍生的合成转化，以证明该方案的实际效用。

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.