Access to Chiral Bridged Biaryls via Brønsted Acid-Catalyzed Asymmetric Addition of Alcohols to Fluoroalkylated Biaryl Oxazepines

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-24 DOI:10.1021/acs.orglett.4c04813

Bowen Zhu, Wei Yuan, Ting Tu, Guimei Dai, Liejin Zhou, Shichao Ren, Xing Yang

引用次数: 0

Abstract

We disclose herein a chiral phosphoric-acid-catalyzed enantioselective addition reaction of alcohols to fluoroalkylated biaryl 1,3-oxoazepines, which furnished a wide range of bridged biaryls bearing a fluoroalkylated quaternary carbon stereocenter on the seven-membered ring in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). Our method can be used for the modification of several natural products and bioactive molecules. Preliminary studies revealed that the products obtained in this reaction exhibit good in vitro bioactivities against two plant pathogens.

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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.