Ni(II)-Catalyzed Site- and Regioselective α-Alkenylation of Cyclic Ketones with Alkenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-29 DOI:10.1021/acs.orglett.5c00745

Tongtong Ni, Xuefeng Xu, Man Cao, Mengfan Chang, Wenguang Li, Xu Zhang, Fengyun Su, Ting Li

引用次数: 0

Abstract

Herein, a nickel-catalyzed α-alkenylation reaction of asymmetric cyclic ketones at the sterically hindered α-position with alkenes is disclosed. The high regioselectivity might originate from the acid-catalyzed enolization reaction, selectively generating the thermodynamically favored enol. The nickel catalyst facilitates the preferential alkenylation of polysubstituted enolates rather than monosubstituted enolates, thereby reversing the conventional regioselectivity of alkenylation at the α-position of ketones. This method encompasses a broad range of applicable substrates of alkenes.

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Ni(II)-催化环酮与烯烃的位点选择性和区域选择性α-烯化反应

本文公开了一种镍催化的不对称环酮在位阻α-位与烯烃的α-烯化反应。高区域选择性可能源于酸催化的烯醇化反应，选择性地生成热力学上有利的烯醇。镍催化剂有利于多取代烯醇酸酯而非单取代烯醇酸酯的优先烯基化，从而逆转了酮类α-位置的传统烯基化区域选择性。该方法包括广泛适用的烯烃底物。

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.