Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots

References

• Bianchi P, Varela RF, Bianchi DA, Kemppainen M, Iribarren AM, Lewkowicz E. 2017. Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones. Process Biochem. 58:137–144.
   Web of Science ®Google Scholar
• Blanchard N, de Weghe PV. 2006. Daucus carota L. mediated bioreduction of prochiral ketones. Org Biomol Chem. 4(12):2348–2353.
   PubMed Web of Science ®Google Scholar
• Brown HC, Prasad JVNV, Zee SH. 1985. Hydroboration. 71. Hydroboration of representative heterocyclic olefins with borane-methyl sulfide, 9-borabicyclo[3.3.1]nonane, dicyclohexylborane, and disiamylborane. J Org Chem. 50(10):1582–1589.
   Web of Science ®Google Scholar
• Brown HC, Vara Prasad JVN. 1986. Chiral synthesis via organoboranes. 6. Hydroboration. 74. Asymmetric hydroboration of representative heterocyclic olefins with diisopinocampheylborane. Synthesis of heterocyclic boronates and heterocyclic alcohols of very high enantiomeric purity. J Am Chem Soc. 108(8):2049–2054.
   Web of Science ®Google Scholar
• Chen Y, Ma B, Cao S, Wu X, Xu Y. 2019. Efficient synthesis of Ibrutinib chiral intermediate in high space-time yield by recombinant E. coli co-expressing alcohol dehydrogenase and glucose dehydrogenase. RSC Adv. 9(4):2325–2331.
   Web of Science ®Google Scholar
• Cho BT. 2009. Recent development and improvement for boron hydride-based catalytic asymmetric reduction of unsymmetrical ketones. Chem Soc Rev. 38(2):443–452.
   PubMed Web of Science ®Google Scholar
• Da Costa MR, Omori AT. 2017. Tween® 20-enhanced bioreduction of acetophenones promoted by daucus carota root. Food Technol Biotech. 55(2):231–235.
   PubMed Web of Science ®Google Scholar
• Dai Y, Shao J, Yang S, Sun B, Liu Y, Ning T, Tian HJ. 2015. Enantioselective syntheses and sensory properties of 2-methyl-tetrahydrofuran-3-thiol acetates. J Agric Food Chem. 63(2):464–468.
   PubMed Web of Science ®Google Scholar
• Duguet N, Petit SM, Marchand P, Harrison-Marchand A, Maddaluno J. 2008. Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi. J Org Chem. 73(14):5397–5409.
   PubMed Web of Science ®Google Scholar
• Erythropel HC, Zimmerman JB, de Winter TM, Petitjean L, Melnikov F, Lam CH, Lounsbury AW, Mellor KE, Janković NZ, Tu Q, et al. 2018. The Green ChemisTREE: 20 years after taking root with the 12 principles. Green Chem. 20(9):1929–1961.
   Web of Science ®Google Scholar
• Fasan R, Kan SBJ, Zhao H. 2019. A continuing career in biocatalysis: Frances H. Arnold. ACS Catal. 9(11):9775–9788.
   PubMed Web of Science ®Google Scholar
• Ghosh AK, Brindisi M. 2015. Organic carbamates in drug design and medicinal chemistry. J Med Chem. 58(7):2895–2940.
   PubMed Web of Science ®Google Scholar
• Keijer T, Bakker V, Slootweg JC. 2019. Circular chemistry to enable a circular economy. Nat Chem. 11(3):190–195.
   PubMed Web of Science ®Google Scholar
• Konuki K, Nagai H, Ito M, Sameshima T. 2014. Process for producing optically active (r)-tetrahydrothiophene-3-ol with high optical purity and high purity: bioconversion and crystallization. Org Process Res Dev. 18(2):310–314.
   Web of Science ®Google Scholar
• Lacheretz R, Pardo DG, Cossy J. 2009. Daucus carota mediated-reduction of cyclic 3-oxo-amines. Org Lett. 11(6):1245–1248.
   PubMed Web of Science ®Google Scholar
• Liang J, Mundorff E, Voladri R, Jenne S, Gilson L, Conway A, Krebber A, Wong J, Huisman G, Truesdell S, et al. 2010. Highly enantioselective reduction of a small heterocyclic ketone: biocatalytic reduction of tetrahydrothiophene-3-one to the corresponding (R)-alcohol. Org Process Res Dev. 14(1):188–192.
   Web of Science ®Google Scholar
• Lihammar R, Millet R, Bäckvall J-E. 2011. An efficient dynamic kinetic resolution of N-Heterocyclic 1,2-amino alcohols. Adv Synth Catal. 353(13):2321–2327.
   Web of Science ®Google Scholar
• Majewska E, Kozłowska M. 2013. Regio- and stereoselective reduction of trans-4-phenylbut-3-en-2-one using carrot, celeriac, and beetroot enzyme systems in an organic solvent. Tetrahedron Lett. 54(47):6331–6332.
   Web of Science ®Google Scholar
• Nemia MMB, Lee J, Joullié MM. 1983. Synthetic routes to 3-pyrrolidinol. Synth Comm. 13(13):1117–1123.
   Web of Science ®Google Scholar
• Oliveira CS, Andrade KT, Omori AT. 2013. One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media. J Mol Cat B Enzymatic. 91:93–97.
   Google Scholar
• Omori AT, Capeletto MG, Yamamoto DY, Filho REO. 2020. A renewable catalyst for a renewable chemical: gram-scale conversion of furfural to furfuryl alcohol by the carrot (Daucus carota). Quim Nova. 43(1):32–36.
   Web of Science ®Google Scholar
• Omori AT, Oliveira CS, Andrade KT, Capeletto MG. 2015. Sassafras oil, carrot bits and microwaves: green lessons learned from the formal total synthesis of (–)-talampanel. RSC Adv. 5(125):103563–103565.
   Web of Science ®Google Scholar
• Sheldon RA, Brady D, Bode ML. 2020. The Hitchhiker’s guide to biocatalysis: recent advances in the use of enzymes in organic synthesis. Chem Sci. 11(10):2587–2605.
   PubMed Web of Science ®Google Scholar
• Sun Z, Lonsdale R, Ilie A, Li G, Zhou J, Reetz MT. 2016. Catalytic asymmetric reduction of difficult-to-reduce ketones: triple-code saturation mutagenesis of an alcohol dehydrogenase. ACS Catal. 6(3):1598–1605.
   Web of Science ®Google Scholar
• Wang C, Wu X, Xiao J. 2008. Broader, greener, and more efficient: recent advances in asymmetric transfer hydrogenation. Chem Asian J. 3(10):1750–1770.
   PubMed Web of Science ®Google Scholar
• Xiong W, Wang X, Kong L. 2015. Design and application of a biphasic system that enhances productivity of Daucus carota-catalyzed asymmetric reduction. Biotechnol Lett. 37(8):1703–1709.
   PubMed Web of Science ®Google Scholar