Stereoselective Arene-Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo-1,2-naphthylenes
Stereoselective Arene-Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo-1,2-naphthylenes
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DOI：
10.1002/anie.201510259
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发表时间：
2016-02-18
影响因子：
16.6
通讯作者：
Sparr, Christof
中科院分区：
文献类型：
--
作者：
Lotter, Dominik;Neuburger, Markus;Sparr, Christof
结构明确的低聚物是天然分子系统功能的基础，也是合成对应物设计的关键。在此，我们描述了一种策略，用于有效地合成的个别立体异构体的1，2-萘低聚物的迭代积木添加和连续的立体选择性芳烃形成羟醛缩合反应。催化剂控制的atropoenantiomeroselective和底物控制的atropoenantiomeroselective羟醛缩合反应提供了结构上不同的叔萘和四萘立体异构体，其代表构型稳定的类似物，否则立体动力学，螺旋形状的邻苯。
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.