Logotheti Maria, Gehres Susanne, França Alexandre S, Bornscheuer Uwe T, de Souza Rodrigo O M A, Höhne Matthias
Department of Biotechnology & Enzyme Catalysis, Institute of Biochemistry, University of Greifswald, Felix-Hausdorff-Str., 4, 17487 Greifswald, Germany.
Biocatalysis and Organic Synthesis Group, Federal University of Rio de Janeiro, Chemistry Institute, 21941909 Rio de Janeiro, Brazil.
J Org Chem. 2025 Jan 17;90(2):1036-1043. doi: 10.1021/acs.joc.4c02228. Epub 2025 Jan 8.
Chiral heterocyclic alcohols and amines are frequently used building blocks in the synthesis of fine chemicals and pharmaceuticals. Herein, we report a one-pot photoenzymatic synthesis route for -Boc-3-amino/hydroxy-pyrrolidine and -Boc-4-amino/hydroxy-azepane with up to 90% conversions and >99% enantiomeric excess. The transformation combines a photochemical oxyfunctionalization favored for distal C-H positions with a stereoselective enzymatic transamination or carbonyl reduction step. Our study demonstrates a mild and operationally simple asymmetric synthesis workflow from easily available starting materials.
手性杂环醇和胺是精细化学品和药物合成中常用的结构单元。在此，我们报道了一种一锅法光酶合成路线，用于合成 -Boc-3-氨基/羟基吡咯烷和 -Boc-4-氨基/羟基氮杂环庚烷，转化率高达90%，对映体过量>99%。该转化过程将有利于远端C-H位置的光化学氧官能化与立体选择性酶促转氨或羰基还原步骤相结合。我们的研究展示了一种从易得的起始原料出发的温和且操作简单的不对称合成工作流程。
