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39.4.2.1.2.3.2 Variation 2: Kinetic Resolution

DOI: 10.1055/sos-SD-039-00359

García Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J.Science of Synthesis, (200839336.

The kinetic resolution of dialkyl sulfoxides is achieved by their oxidation with different reagents. Good results are obtained in the solid state in the presence of an optically active host compound.[‌555‌,‌556‌] The process proceeds via a combination of enantioselective inclusion complexation and selective oxidation in the solid state. Thus, racemic sulfoxides react with substoichiometric amounts of 3-chloroperoxybenzoic acid in the presence of ()-1,6-bis(2-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol, affording the corresponding sulfone and optically enriched unreacted sulfoxide (Scheme 115). In some cases, the use of magnesium monoperoxyphthalate, instead of 3-chloroperoxybenzoic acid, improves the results.

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M8 Meeeeeeee Meeee ee (%) Meeee (%) Mee
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(MM8)8Me MMMMM 88 88 [‌888‌]
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M8 Meeeee ee (%) (Meeeee) Mee
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Me eeeeeeeeeeeeeee 88 (M) [‌888‌]
Me eeeeeeee 88 (M) [‌888‌]
Me eeeeeeeeeeeeeee 88 (M) [‌888‌]

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References


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