碱促进的亚烷基琥珀酰亚胺级联乙烯基迈克尔/迈克尔加成反应，用于构建五代环戊烷。

IF 2.8 3区化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-10-09 DOI:10.1039/d4ob01455c

Peiyao Liang , Siyi Chen , Xin Liu , Shenghan Teng , Shoulei Wang

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引用次数: 0

摘要

在此，我们成功开发了一种高效的碱催化级联乙烯基迈克尔/迈克尔环加成反应，用于α-亚烷基琥珀酰亚胺与吲哚衍生吡唑酮的反应。该反应以良好的收率、优异的非对映选择性和独有的乙烯基位点选择性获得了多种与螺吲哚融合的高官能度环戊烷。这一策略是 α-亚烷基琥珀酰亚胺作为亲核试剂引发乙烯基级联反应的首个实例。

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Base-promoted cascade vinylogous Michael/Michael addition of alkylidene succinimides for the construction of penta-substituted cyclopentanes†

Herein, an efficient, base catalyzed cascade vinylogous Michael/Michael cycloaddition reaction of α-alkylidene succinimides and oxindole-derived pyrazolones has been successfully developed. A variety of highly functionalized cyclopentanes fused with spirooxindoles were obtained in good yields, with excellent diastereoselectivities and exclusive vinylogous site-selectivities. This strategy represents the first example of α-alkylidene succinimides serving as nucleophilic reagents to trigger a vinylogous cascade reaction.

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来源期刊

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.