钯催化的 3-硝基吲哚与 2-乙烯基环丙烷-1,1-二羧酸酯的去芳构化[3 + 2]环加成反应。
Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates.
机构信息
School of Chemistry, University of Wollongong , Wollongong, New South Wales 2522, Australia.
School of Physical Sciences - Chemistry, University of Tasmania , Hobart, Tasmania 7001, Australia.
出版信息
J Org Chem. 2017 Dec 15;82(24):13517-13529. doi: 10.1021/acs.joc.7b02624. Epub 2017 Dec 4.
A trans-diastereoselective Pd-catalyzed dearomative [3 + 2] cycloaddition between vinylcyclopropane dicarboxylates and 3-nitroindoles has been developed. The reaction provides densely functionalized cyclopenta[b]indolines with versatile vinyl and nitro-groups. The addition of a halide additive was found to be critical for the diastereoselectivity of the reaction, which is proposed to be a result of a rapid π-σ-π interconversion between the intermediates allowing for Curtin-Hammett control. A switch in diastereoselectivity to afford products with the vinyl and nitro groups cis to each other is observed with a 4-substituted 3-nitroindole.
发展了一种钯催化的反式非对映选择性乙烯基环丙烷二羧酸酯与 3-硝基吲哚的去芳构化[3+2]环加成反应。该反应提供了具有多种乙烯基和硝基官能团的稠合环戊并[b]吲哚啉。发现添加卤化物添加剂对于反应的非对映选择性至关重要，这被认为是中间体之间快速的π-σ-π转换的结果，允许 Curtin-Hammett 控制。用 4-取代的 3-硝基吲哚观察到反式非对映选择性的转变，得到了乙烯基和硝基基团彼此顺式的产物。
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