Schiral sulfoximines

Two types of sulfoximinocarboxylates (analogous to sulfinylcarboxylates 16), namely S-aryl-S-methoxycarbonylmethyl-N-methyl sulfoximine 36 and S-methyl-S-phenyl-N-ethoxycarbonyl sulfoximine 37, were subjected to hydrolysis in the presence of PLE in a phosphate buffer. As a result of a kinetic resolution, both the enantiomerically enriched recovered substrates and the products of hydrolysis and subsequent decarboxylation 38 and 39, respectively, were obtained with moderate to good ees (Equations 20 and 21). Interestingly, in each case the enantiomers of the substrates, having opposite spatial arrangement of the analogous substituents, were preferentially hydrolysed.50 This was explained in terms of the Jones PLE active site model.51

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