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Please login to access the full content or check if you have access via2.6.3.4.1 Other Chiral Monosubstituted Epoxides
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Wohlgemuth, R., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 543.
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]
Meeeee 88 Meeeeee Meeeeeeee Meeeeeeee Meeeeee Meeeeeeeee ee Meeeeeeeeeeeee Meeeeeeeeeeee[88–88]
M8 | M8 | ee (%) ee (M)-88 | Meeee (%) ee (M)-88 | Mee |
---|---|---|---|---|
Me | Me | >88 | 88.8 | [88] |
eMe | eMe | >88 | 88 | [88] |
MM8MMe8MM8 | >88 | 88.8 | [88] |
References
[77] | Meeeèeee, M.; Meeeeeee, M.; Meeeeeee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[78] | Meéeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeee, M., Mee. M. Mee. Meee., (8888), 8888. |
[79] | Meee, M. M.; Meee, M. M.; Mee, M. M.; Me, M. M., Meee. Meeeeeeee. Meeeeeeeee., (8888) 88, 88. |