We have studied the proline-directed, Pd-catalyzed enantioselective hydrogenation of isophorone in the liquid state using a variety of methods. Our results unambiguously reveal the true reaction pathway and demonstrate that all earlier mechanistic hypotheses are wrong: although a proline/isophorone condensation product is formed, it is merely a spectator and not a key reaction intermediate in subsequent heterogeneous hydrogenation. Enantioselectivity is the result of kinetic resolution-a proc...Expand abstract
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Heterogeneously catalyzed asymmetric C=C hydrogenation: origin of enantioselectivity in the proline-directed Pd/isophorone system.
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