Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale
Kärki, K., Siitonen, J., Kortet, S., Cederström, M., & Pihko, P. (2018). Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale. Synlett, 29(13), 1723-1728. https://doi.org/10.1055/s-0037-1610109
© Georg Thieme Verlag, 2018.
The chiral building block 3-oxodicyclopentadiene (1) can be readily resolved on a decagram scale by a short sequence consisting of (1) reduction to the corresponding endo-alcohol, (2) enzymatic oxidative resolution with a ketoreductase enzyme to give (+)-1 and the (+)-form of the endo-alcohol, and (3) reoxidation of the (+)-endo-alcohol with another ketoreductase to give (–)-1. With a selectivity factor of 310, the enantiomeric ratios of the resolved (+)-endo-alcohol and (+)-ketone are both >99:1. Both enzymatic oxidations could be performed with a at least 300:1 substrate/catalyst ratio (w/w).
PublisherGeorg Thieme Verlag
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