Abstract
We report a comprehensive model surface science study, using scanning tunneling microscopy (STM), of the regioselective and stereospecific complexation of a prochiral substrate molecule to a chiral modifier molecule on a metal surface. The system is chosen so as to compare the prochiral ratio (pr) measured directly by STM for the model system with the reported enantiomeric ratio (er) for the hydrogenation of the prochiral molecule using the same chiral modifier and metal under true reaction conditions. Specifically, diastereomeric complexes formed between ketopantolactone (KPL) and (R)-1-(1-naphthyl)ethylamine ((R)-NEA) on Pt(111) were studied as a function of the ratio of KPL to (R)-NEA. Only KPL molecules in complexes are detected in the STM experiments, performed between 237 and 250 K, due to rapid diffusion of free KPL on the surface. The prochirality of KPL in almost all bimolecular and termolecular, (KPL)2/(R)-NEA, complexation configurations is assigned as pro-R or pro-S using the contrast within t...
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