Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale,Synlett

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Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale
Synlett ( IF 1.7 ) Pub Date : 2018-06-22 , DOI: 10.1055/s-0037-1610109
Petri Pihko ₁ , Katja Kärki ₁ , Juha Siitonen , Sami Kortet ₁ , Mona Cederström ₁

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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).

中文翻译：

3-氧代二环戊二烯的十克级酶促拆分

手性构件 3-氧代二环戊二烯 (1) 可以很容易地在十克规模上通过短序列拆分，包括 (1) 还原为相应的内醇，(2) 用酮还原酶进行酶促氧化拆分，得到 (+) - 1 和内醇的 (+)-形式，以及 (3) (+)- 内醇与另一种酮还原酶再氧化得到 (-)- 1 。在选择性因子为 310 的情况下，已解析的 (+)- 内醇和 (+)- 酮的对映体比率均 > 99:1。两种酶促氧化都可以以至少 300:1 的底物/催化剂比 (w/w) 进行。

更新日期：2018-06-22

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