The adsorption of R- and S-2-butanol is studied on l -proline modified Pd(111) surfaces. It is found that l -proline modifies the chemistry of 2-butanol such that it predominantly adsorbs and desorbs reversibly with a few percent reacting to form 2-butoxide species. The chemisorptive enantioselectivity ratio, defined as the S -2-butanol coverage divided R -2-butanol coverage, varies with the amount of l -proline on the surface and reaches a maximum of ∼1.2 at an l -proline coverage of ∼0.2. The enantioselectivity of 2-butoxide hydrogenation by adsorbed deuterium is measured and reaches a maximum of ∼1.9, also at an l -proline coverage of 0.2 indicating that both reaction and adsorption occur enantioselectively.
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Gao et al. (2008) studied this question.