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在NHC催化下实现的涉及烯醛和2-硝基苯并呋喃的脱芳构化迈克尔加成反应。

Dearomative Michael addition involving enals and 2-nitrobenzofurans realized under NHC-catalysis.

作者信息

Dyguda Mateusz, Skrzyńska Anna, Sieroń Lesław, Albrecht Łukasz

机构信息

Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.

Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, Łódź, 90-924, Poland.

出版信息

Chem Commun (Camb). 2022 Apr 28;58(35):5367-5370. doi: 10.1039/d2cc00294a.

Abstract

In this manuscript, the first enantioselective dearomative Michael addition between α,β-unsaturated aldehydes and 2-nitrobenzofurans realized under N-heterocyclic carbene activation has been described. The reaction proceeds addition of homoenolate to Michael acceptors leading to the formation of biologically important heterocycles with high yields and stereoselectivities. Their functionalization potential has been confirmed in selected, diastereoselective transformations.

摘要

在本论文中,描述了在氮杂环卡宾活化作用下实现的α,β-不饱和醛与2-硝基苯并呋喃之间的首例对映选择性去芳构化迈克尔加成反应。该反应通过向迈克尔受体加成高烯醇盐进行,从而以高收率和立体选择性生成具有生物学重要性的杂环化合物。它们的官能化潜力已在选定的非对映选择性转化反应中得到证实。

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