Visible‐Light‐Enabled Dual‐Catalysis Approach to Stereoselective [2+2] Cycloaddition of Erlenmeyer‐Plöchl Azlactones

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-11-01 DOI:10.1002/ajoc.202400271

Dr. Isabella F. S. Marra , Ms. Larissa P. Silva , Dr. Pedro P. De Castro , Dr. Leonã S. Flores , Dr. Kleber T. De Oliveira , Dr. Paulo E. N. De Souza , Dr. Brenno A. D. Neto , Dr. Hélio F. Dos Santos , Dr. Giovanni W. Amarante

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引用次数: 0

Abstract

Visible‐light‐driven dual catalysis was employed to stereoselectively produce densely substituted cyclobutanes from Erlenmeyer‐Plöchl azlactones. The single‐step preparation of non‐natural amino acid dimers containing the cyclobutane moiety was achieved through a synergy between iridium photocatalysis and catalytic nickel(II) triflate as a Lewis acid. The desired 1,2‐(zeta)‐Z,E‐isomers were isolated in good yields and with high regio‐ and diastereoselectivity (in all cases, >19 : 1 d.r.). To the best of our knowledge, this is the first report of direct access to truxinic acid analogues using azlactones. Control experiments, EPR reaction monitoring, and DFT calculations suggest that the presence of a Lewis acid, combined with the use of powerful blue LEDs, plays a crucial role in the reactivity of this reaction.

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利用可见光的双催化方法实现埃伦梅尔-普洛尔氮杂环内酯的立体选择性 [2 + 2] 环加成反应

利用可见光驱动的双重催化作用，从 Erlenmeyer-Plöchl 氮内酯中立体选择性地制备出了密集取代的环丁烷。通过铱光催化与作为路易斯酸的催化三镍(II)之间的协同作用，实现了含有环丁烷分子的非天然氨基酸二聚体的一步制备。所需的 1,2-（zeta）-Z,E-异构体以良好的产率和高区域及非对映选择性（在所有情况下均为 19:1 d.r.）分离出来。据我们所知，这是首次报道利用氮内酯直接获得曲辛酸类似物。对照实验、EPR 反应监测和 DFT 计算表明，路易斯酸的存在以及强力蓝光 LED 的使用，对这一反应的反应性起着至关重要的作用。

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

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.