布氏酸催化 [4 + 2] 环加成法合成具有抗真菌活性的双苯甲酮类螺环酮类化合物。

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC
Teng Hu , Yuxuan Zhao , Xiaoyan Luo , Zhong Li , Wu-Lin Yang
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引用次数: 0

摘要

在 CF3CO2H 催化下,实现了邻羟基苄醇与异色酮的分子间 [4 + 2] 环加成反应。在无金属的温和条件下,生成了范围广泛的双苯并[6,6]-螺酮,收率从中等到极佳(45-98%),非对映选择性大多极佳(最高可达 >20 : 1 dr)。此外,还对对映体选择性进行了初步研究,在 Sc(OTf)3/Feng 的手性 N,N'-二氧化配体存在下,获得了双苯annulated [6,6]-spiroketal ,ee 为 61%。一些双苯注烷[6,6]-螺环酮类产品在体外对硬皮病菌和根瘤菌表现出良好的抗真菌活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities†

Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities†

Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities†

The intermolecular [4 + 2] cycloaddition of o-hydroxy benzyl alcohols with isochroman ketals was realized by CF3CO2H catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45–98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)3/Feng's chiral N,N′-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good in vitro antifungal activities against Sclerotinia sclerotiorum and Rhizoctonia solani.

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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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