Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1344530 | Tetrahedron: Asymmetry | 2010 | 7 Pages |
The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1-methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1,2-diol and its antipodal (R)-epoxide in high ees.
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(R)-1-Benzyloxymethyl-1-vinyloxiraneC12H14O2Ee = 82.9%[α]D24=+28.9 (c 1.12, MeOH)Source of chirality: Bacillus subtilis epoxide hydrolase-catalysed hydrolysisAbsolute configuration: (R)
(R)-2-Benzyloxymethyl-3-butene-1,2-diolC12H16O3Ee = 97.7%[α]D24=-28.1 (c 0.65, CH2Cl2)Source of chirality: Bacillus subtilis epoxide hydrolase-catalysed hydrolysisAbsolute configuration: (R)