手性吡啶鎓盐的 N-杂环卡宾催化亲核酰化去芳构化反应
Enantioselective Dearomatization of Alkylpyridiniums by N-Heterocyclic Carbene-Catalyzed Nucleophilic Acylation.
机构信息
Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Ferrara , Via L. Borsari, 46, I-44121 Ferrara, Italy.
Dipartimento di Chimica Industriale "Toso Montanari", Università di Bologna , V. Risorgimento 4, I-40136 Bologna, Italy.
出版信息
J Org Chem. 2018 Feb 16;83(4):2050-2057. doi: 10.1021/acs.joc.7b02996. Epub 2018 Jan 27.
A chiral NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and enantioselectivities in the range 52-78% ee. The (4R)-absolute configuration of the synthesized compounds has been determined by the TD-DFT simulation of the electronic circular dichroism spectra.
一种手性 NHC 催化的活化 N-烷基吡啶鎓盐与脂肪醛的去芳构化反应被描述。所得酰化的 1,4-二氢吡啶以完全的 C4 区域选择性和 52-78%ee 的对映选择性获得。通过对电子圆二色性光谱的 TD-DFT 模拟，确定了合成化合物的（4R）绝对构型。
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