Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2-epoxycyclohexane: the synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol

Biocatalysis of Deracemization in 1,2-Diols

“…Other potential racemic precursors to indanediol, including 1bromoindan-2-one (±)-(4), trans-2-bromoindan-1-ol (±)-(5), indene oxide (±)-(6), and 2-hydroxyindan-1-one (±)- (7), were also found to be successful substrates under our reaction conditions. The results obtained upon incubation of each of the substrates with C. cassiicola are indicated in the table.…”

“…Bakers' yeast has been shown to reduce a-hydroxy ketones with excellent enantioselectivities, 3,5 racemic 1,2diols can be resolved by lipase catalysed transesterification, 6 and epoxides can be hydrolysed by enzymes. 7 Microbial stereoinversion and dynamic resolution have now become valuable and versatile synthetic tools. 8 Reports of secondary alcohol stereoinversion either by single cell 9 or combined microorganism systems 10 have appeared sparingly over the past decade, but diol stereoinversions are scarce.…”

Niobium Pentachloride Catalysed Ring Opening of Epoxides

“…The relative stereochemistry of compounds 6 , 7 and 9 was assigned based on their 1 H- and 13 C-NMR spectra, and careful comparison with literature data [ 5 ]. For compounds 8 and 10 , however, no literature data was available.…”

Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

“…In addition, one trisubstituted racemic epxoide, 1-methyl-1,2-epoxy-cyclohexane, has also been transformed to the corresponding (1S, 2S)-diol, leaving the (1S, 2R)-epoxide unchanged with >99% ee and 30% yield with the whole cell of Corynebacterium C12 containing EH [188]. This type of substrate has not been reported for the Jacobsen's HKR.…”