d'Aleman Antoine, Gayraud Oscar, Fressigné Catherine, Petit Emilie, Bailly Laetitia, Maddaluno Jacques, De Paolis Michaël
COBRA, Normandie University 76000 Rouen France
Chem Sci. 2023 Jan 27;14(8):2107-2113. doi: 10.1039/d2sc06842g. eCollection 2023 Feb 22.
The lactonization of 2-(2-nitrophenyl)-1,3-cyclohexanediones containing an alcohol side chain and up to three distant prochiral elements is reported by isomerization under the mediation of simple organocatalysts such as quinidine. Through a process of ring expansion, strained nonalactones and decalactone are produced with up to three stereocenters in high er and dr (up to 99 : 1). Distant groups, including alkyl, aryl, carboxylate and carboxamide moieties, were examined.
报道了在奎尼丁等简单有机催化剂的介导下，通过异构化反应实现含有醇侧链且最多有三个远程前手性元素的2-(2-硝基苯基)-1,3-环己二酮的内酯化反应。通过扩环过程，生成了具有高达三个立体中心的张力九元内酯和十氢化萘内酯，其对映体过量值（ee）和非对映体比例（dr）高达99:1。研究了包括烷基、芳基、羧酸盐和羧酰胺部分在内的远程基团。
