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Stereoselective access to β‐gem‐difluorinated alcohols through enzymatic reduction
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2024-04-17 , DOI: 10.1002/adsc.202400330
Lucas Bacheley 1 , Julien Boutet 2 , Gérard Guillamot 3 , Pierre Gilles 4 , Juliette Martin 5 , Phannarath Phansavath 6 , Virginie Ratovelomanana-Vidal 6
Affiliation  

We report here a mild and efficient process to access diversely functionalized enantioenriched b‐gemdifluorinated (S)‐alcohols by using biocatalytic reduction in > 99% yield and enantiomeric excesses ranging from 96% to >99%. This novel approach involves enzymatic reduction of α‐gem‐difluorinated heterocyclic and carbocyclic ketone derivatives as well as an acyclic gem‐difluorinated β‐ketosulfone and proceeds under mild conditions at room temperature under aqueous conditions to produce a range of high added value enantioenriched difluorinated alcohols including 3,3‐difluorochromanol, 3,3‐difluorothiochromanol, 3,3‐difluoro‐dihydroquinolinol, and α‐difluorinated β‐hydroxysulfone derivatives. A comparative study between enzymatic reduction and metal‐catalyzed asymmetric transfer hydrogenation was carried out as well.

中文翻译:

通过酶促还原立体选择性获得β-宝石-二氟化醇

我们在这里报告了一种温和而有效的方法,通过使用生物催化还原来获得多种功能化的对映体富集的b-二氟化(S)-醇,产率> 99%,对映体过量范围为96%至> 99%。这种新方法涉及α-偕二氟化杂环和碳环酮衍生物以及无环偕二氟化β-酮砜的酶促还原,并在室温和水性条件下温和条件下进行,产生一系列高附加值的对映体富集的二氟化醇包括3,3-二氟苯并二氢苯并二氢吡喃醇、3,3-二氟二氢苯并二氢苯并吡喃醇、3,3-二氟二氢喹啉醇和α-二氟化β-羟基砜衍生物。还对酶还原和金属催化不对称转移氢化进行了比较研究。
更新日期:2024-04-17
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