The synthesis and characterization of a number of chiral complexes of the type [(P−P)Pt(μ-OH)]2
2+ (P−P = (R)-binap, (S,S)-diop, (R,R)-pyrphos, (R,R)-norphos, (R,R)-Me-duphos,
(S,S)-bppm) are reported. These are used for the enantioselective Baeyer−Villiger oxidation
of substituted meso-cyclohexanones using 35% hydrogen peroxide as oxidant. The reaction
is performed at 0 °C with moderate yields, showing in some cases ee higher than 50%. Best
catalysts are those containing atropoisomeric ligands possessing C
2 symmetry and/or capable
of making seven-membered chelate rings with the metal. The results represent the first
example of dissymmetrization of achiral cyclohexanones obtained via the Baeyer−Villiger
oxidation using a transition metal catalyst.
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