通过分子间氧化还原行为实现的外消旋化和去外消旋化
Racemization and Deracemization through Intermolecular Redox Behaviour.
作者信息
Engwerda Anthonius H J, Meekes Hugo, Bickelhaupt F Matthias, Rutjes Floris P J T, Vlieg Elias
机构信息
Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ, Nijmegen, The Netherlands.
Department of Theoretical Chemistry and Amsterdam Center, for Multiscale Modeling, VU University, De Boelelaan 1083, 1081 HV, Amsterdam, The Netherlands.
出版信息
Chemistry. 2019 Jul 22;25(41):9639-9642. doi: 10.1002/chem.201902438. Epub 2019 Jul 1.
Chiral molecules exhibiting a quinone and/or hydroquinone moiety are ubiquitous in natural products and small molecule drugs. Herein, we describe a chiral quinone-hydroquinone molecule that racemizes through a reversible redox reaction. Using a combined computational and experimental approach, we show that this racemization proceeds via an intermolecular reaction mechanism. Starting from two achiral reactants, this molecule could be obtained in enantiopure form using Viedma ripening.
含有醌和/或对苯二酚部分的手性分子在天然产物和小分子药物中普遍存在。在此，我们描述了一种通过可逆氧化还原反应发生外消旋化的手性醌-对苯二酚分子。使用计算和实验相结合的方法，我们表明这种外消旋化通过分子间反应机制进行。从两种非手性反应物开始，使用维德马熟化法可以以对映体纯的形式获得这种分子。
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