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碱促进的亚烷基琥珀酰亚胺的串联乙烯型迈克尔/迈克尔加成反应用于构建五取代环戊烷。

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

作者信息

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

机构信息

Strait Institute of Flexible Electronics (SIFE, Future Technologies), Fujian Key Laboratory of Flexible Electronics, Fujian Normal University and Strait Laboratory of Flexible Electronics (SLoFE), Fuzhou 350117, China.

出版信息

Org Biomol Chem. 2024 Nov 21;22(45):8832-8837. doi: 10.1039/d4ob01455c.

DOI:10.1039/d4ob01455c
PMID:39405033
Abstract

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.

摘要

在此,已成功开发出一种高效的、碱催化的α-亚烷基琥珀酰亚胺与吲哚酮衍生的吡唑啉酮的串联乙烯型迈克尔/迈克尔环加成反应。以良好的产率、优异的非对映选择性和独特的乙烯型位点选择性得到了多种与螺吲哚酮稠合的高度官能化环戊烷。该策略代表了α-亚烷基琥珀酰亚胺作为亲核试剂引发乙烯型串联反应的首例。

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