Other Cchiral organosulfur compounds

Desymmetrization of meso-3,4-dihydroxythiolane 13 was accomplished either via its lipase-catalysed acetylation or hydrolysis of the corresponding diacetate 15. Each method led to the opposite enantiomer of the monoacetate 14 (Equation 11).33 It is noteworthy that, although the resulting monoacetate 14 exhibited only a low to moderate enantiomeric excess (up to 36%), it turned out to be configurationally relatively stable in contrast to its carba-analogue, ds-1-acetoxy-2-hydroxycyclopentane, which was found to undergo fast racemization due to a 1,2-acetyl shift.

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