Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of TETRAHYDROPYRAN-2-METHANOL (cas 100-72-1)

Add time:07/19/2019    Source:sciencedirect.com

(±)-Tetrahydropyran-2-methanol (1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)-3 to (R)-(−)-3 (ee ⩾ 99%). The antipodal alcohol (S)-(+)-1 (ee ⩾ 95%) was obtained after recycling of the moderately S-enriched 1 to the butyrate ester 3 and subsequent hydrolysis. A fourfold increase in enantioselectivity (E value = 24) was observed when hydrolysis was performed using one of the fractions. Tetrahydrofurfuryl alcohol (2) could not be resolved since the best selectivity attained was E = 3.1 from hydrolysis by the lipase B of Candida antarctica. Resolution by transesterification was found to be unsuitable for both compounds.

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