Diastereoselective thia-[3 + 2] cyclization of acetylpyranuloses and β-oxodithioesters†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-01-31 DOI:10.1039/D5OB00022J
Shihao Cheng, Xiao Ni, Guanyou Cui, Chenhu Dong, Yujie Ma, Jinlong Li, Xiaofeng Bao and Yu Zhao
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Abstract

Acetylpyranuloses and β-oxodithioesters, recognized as notable electrophiles and trinucleophiles, are frequently employed in intricate cyclization reactions. Nevertheless, there is a lack of literature documenting the cyclization products derived from these two reagents. This paper unveils a base-mediated sequential Michael addition and SN2-type cyclization reactions involving acetylpyranuloses and β-oxodithioesters. A total of 23 functionalized bicyclic molecules featuring a thieno[2,3-b] pyran scaffold have been obtained diastereoselectively in moderate to good yields. This novel method could aid in the development of new drugs and enrich the toolbox for synthesizing pharmaceuticals and natural products.

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乙酰吡喃糖和β-氧二硫酯的非对映选择性[3 + 2]环化。
乙酰吡喃糖和β-氧二硫酯被认为是著名的亲电试剂和亲三核试剂,经常用于复杂的环化反应。然而,缺乏文献记录这两种试剂的环化产物。本文揭示了涉及乙酰吡喃糖和β-氧二硫酯的碱基介导的顺序Michael加成反应和sn2型环化反应。共获得了23个具有噻吩[2,3-b]吡喃支架的功能化双环分子,产量中等至较高。这种新方法有助于新药的开发,丰富了合成药物和天然产物的工具箱。
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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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