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2.6.3.4.1 Other Chiral Monosubstituted Epoxides

DOI: 10.1055/sos-SD-215-00303

Wohlgemuth, R.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152543.

Enantiomerically pure acetal-protected glycidaldehyde derivatives (R)- or (S)-11 have been prepared by hydrolytic kinetic resolution using recombinant Aspergillus niger epoxide hydrolases (Scheme 18).[‌77‌] Enantiomerically pure (S)-2-(2,2-diethoxyethyl)oxirane could also be obtained in 30% yield by resolving racemic 2-(2,2-diethoxyethyl)oxirane using crude epoxide hydrolase from Aspergillus niger.[‌78‌] The epoxide hydrolase from Acinetobacter baumannii showed the highest enantioselectivity in the resolution of racemic ethyl 2-(oxiran-2-yl)acetate, and ethyl (R)-2-(oxiran-2-yl)acetate could be obtained in 46% yield and >99% ee.[‌79‌]

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