高温催化下的烯还原酶催化脱对称：全碳季型γ-中心的远程控制

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-13 DOI:10.1021/acs.orglett.4c04383

David A. Petrone, Damien Valette, Olivia Boyd, Justin Newman, Erin Plasek, Guangxin Shao, Xiao Wang, Tetsuji Itoh, Matthew Maddess, Feng Peng

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引用次数: 0

摘要

我们报道了通过烯还原酶（ERED）催化的前手性环己二烯酮的去对称，远程立体控制全碳季γ-中心。通过利用高通量实验（HTE）方案，我们能够在温和的反应条件下快速鉴定出能够使螺环环己二烯酮和非螺环2,6-二取代环己二烯酮底物去对称的EREDs，产率高达85%，具有优异的立体选择性（高达99% ee和20:1 dr）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers

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HTE-Enabled Development of an Ene-Reductase-Catalyzed Desymmetrization: Remote Control of All-Carbon Quaternary γ-Centers

We report the remote stereocontrol of all-carbon quaternary γ-centers via an ene-reductase (ERED)-catalyzed desymmetrization of prochiral cyclohexadienones. By leveraging high-throughput experimentation (HTE) protocols, we were able to rapidly identify EREDs capable of desymmetrizing both spirocyclic cyclohexadienones and non-spirocyclic 2,6-disubstituted cyclohexadienone substrates in up to 85% yield with excellent levels of stereoselectivity (up to >99% ee and >20:1 dr) under mild reaction conditions.

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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.