光诱导非对映选择性和立体发散合成c -苯乙烯基糖苷

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-16 DOI:10.1021/acs.orglett.5c0143710.1021/acs.orglett.5c01437

Jialu Ma, Weitao Yan, Xinyu Chen, Wenxu Zhen, Jin Yu*, Ruo Wang* and Chunfa Xu*,

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引用次数: 0

摘要

介绍了一种新的、高效的通过亚硫酸糖基钠与高价苯乙烯碘试剂反应合成无保护和无保护苯乙烯c -糖苷的立体选择性和立体发散合成方法。以2-溴-9-芴酮为光催化剂，选择性地制备了具有E构型的c -苯乙烯基糖苷。此外，新设计的铱基催化剂的引入使得糖苷主要在Z构型中选择性形成。机制研究表明，糖基自由基参与了转化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photoinduced Diastereoselective and Stereodivergent Synthesis of C-Styryl Glycosides

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Photoinduced Diastereoselective and Stereodivergent Synthesis of C-Styryl Glycosides

A novel and efficient method for the stereoselective and stereodivergent synthesis of both unprotected and protected styryl C-glycosides through the reaction of sodium glycosyl sulfinate and hypervalent styryl iodine reagents is described. Using 2-bromo-9-fluorenone as a photocatalyst, C-styryl glycosides with an E configuration were selectively obtained. Furthermore, the introduction of a newly designed iridium-based catalyst enabled the selective formation of glycosides predominantly in the Z configuration. Mechanistic studies reveal the glycosyl radical is involved in the transformation.

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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.