Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2920-3. doi: 10.1002/anie.201510259. Epub 2016 Jan 21.
Structurally well-defined oligomers are fundamental for the functionality of natural molecular systems and key for the design of synthetic counterparts. Herein, we describe a strategy for the efficient synthesis of individual stereoisomers of 1,2-naphthylene oligomers by iterative building block additions and consecutive stereoselective arene-forming aldol condensation reactions. The catalyst-controlled atropoenantioselective and the substrate-controlled atropodiastereoselective aldol condensation reaction provide structurally distinct ter- and quaternaphthalene stereoisomers, which represent configurationally stable analogues of otherwise stereodynamic, helically shaped ortho-phenylenes.
结构明确的低聚物对于天然分子系统的功能至关重要，也是设计合成类似物的关键。在此，我们描述了一种通过迭代砌块添加和连续的立体选择性芳构化 aldol 缩合反应高效合成 1,2-萘烯低聚物单个立体异构体的策略。催化剂控制的非对映选择性和底物控制的非对映选择性 aldol 缩合反应提供了结构独特的三萘和四萘立体异构体，它们是构象稳定的类似物，而其他的则是立体动态的螺旋形邻苯二烯。
