Synlett 2023; 34(05): 399-404
DOI: 10.1055/s-0042-1751403
synpacts

Cascade Processes Merging Chemical and Enzyme Catalysis

Christian Ascaso-Alegre
a   Institute of Chemical Synthesis and Homogeneous Catalysis (ISQCH) Spanish National Research Council (CSIC), Pedro Cerbuna 12, 50009 Zaragoza, Spain
,
a   Institute of Chemical Synthesis and Homogeneous Catalysis (ISQCH) Spanish National Research Council (CSIC), Pedro Cerbuna 12, 50009 Zaragoza, Spain
b   Aragonese Foundation for Research & Development (ARAID), Zaragoza, Spain
› Author Affiliations
We would like to thank the Agencia Estatal de Investigación (AEI), the Ministerio de Ciencia e Innovación (Ministry of Science and Innovation, MCIN), and the EU for the financial support (PID2020-113351RA-100/AEI/10.13039/501100011033 and TED2021-130803B-I00 MCIN/AEI /10.13039/501100011033 NextGenerationEU/PRTR). J.M-S also thanks the Fundación Agencia Aragonesa para la Investigación y el Desarrollo (Aragonese Foundation for Research & Development, ARAID) for personal funding.


Dedicated to Prof. Vicente Gotor on the occasion of his retirement

Abstract

Cascade processes are an attractive strategy to rapidly build molecular complexity and circumvent the need to isolate reaction intermediates, providing higher efficiencies into synthetic routes with lower environmental toll. We have recently developed a new method to synthesise chiral 1,4-nitro alcohols by sequentially combining three transformations in the same reaction vessel via asymmetric C–C bond formation using a chiral thiourea catalyst and a bioreduction process as key steps.

1 Introduction

2 A Chemoenzymatic Cascade to Make Chiral 1,4-Nitro Alcohols

3 Conclusions and Perspectives



Publication History

Received: 23 November 2022

Accepted after revision: 09 December 2022

Article published online:
10 January 2023

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  • References

  • 1 Yi D, Bayer T, Badenhorst CP. S, Wu S, Doerr M, Höhne M, Bornscheuer UT. Chem. Soc. Rev. 2021; 50: 8003
  • 2 Schrittwieser JH, Velikogne S, Hall M, Kroutil W. Chem. Rev. 2018; 118: 270
  • 3 Ascaso-Alegre C, Mangas-Sánchez J. Eur. J. Org. Chem. 2022; e202200093 DOI: 10.1002/ejoc.202200093.
  • 4 Rudroff F, Mihovilovic MD, Gröger H, Snajdrova R, Iding H, Bornscheuer UT. Nat. Catal. 2018; 1: 12
  • 5 Liu Y, Liu P, Gao S, Wang Z, Luan P, González-Sabín J, Jiang Y. Chem. Eng. J. 2021; 420: 127659
  • 6 Millet R, Träff AM, Petrus ML, Bäckvall JE. J. Am. Chem. Soc. 2010; 132: 15182
  • 7 Simon RC, Busto E, Schrittwieser JH, Sattler JH, Pietruszka J, Faber K, Kroutil W. Chem. Commun. 2014; 50: 15669
  • 8 Baer K, Kraußer M, Burda E, Hummel W, Berkessel A, Gröger H. Angew. Chem. Int. Ed. 2009; 48: 9355
  • 9 Rulli G, Duangdee N, Baer K, Hummel W, Berkessel A, Gröger H. Angew. Chem. Int. Ed. 2011; 50: 7944
  • 10 Schober L, Tonin F, Hanefeld U, Gröger H. Eur. J. Org. Chem. 2022; e202101035 DOI: 10.1002/ejoc.202101035.
  • 11 Suljic S, Pietruszka J, Worgull D. Adv. Synth. Catal. 2015; 357: 1822
  • 12 Wang Y, Wang C, Cheng Q, Su Y, Li H, Xiao R, Tan C, Liu G. Green Chem. 2021; 23: 7773
  • 13 Ascaso-Alegre C, Herrera RP, Mangas-Sánchez J. Angew. Chem. Int. Ed. 2022; 61: 1
  • 14 Mei K, Jin M, Zhang S, Li P, Liu W, Chen X, Xue F, Duan W, Wang W. Org. Lett. 2009; 11: 2864
  • 15 Rufino VC, Pliego JR. Asian J. Org. Chem. 2021; 10: 1472
  • 16 Zhang H, Chuan Y, Li Z, Peng Y. Adv. Synth. Catal. 2009; 351: 2288
  • 17 Cao CL, Ye MC, Sun XL, Tang Y. Org. Lett. 2006; 8: 2901
  • 18 Cao YJ, Lai YY, Wang X, Li YJ, Xiao WJ. Tetrahedron Lett. 2007; 48: 21
  • 19 Huffman MA, Fryszkowska A, Alvizo O, Borra-Garske M, Campos KR, Canada KA, Devine PN, Duan D, Forstater JH, Grosser ST, Halsey HM, Hughes GJ, Jo J, Joyce LA, Kolev JN, Liang J, Maloney KM, Mann BF, Marshall NM, McLaughlin M, Moore JC, Murphy GS, Nawrat CC, Nazor J, Novick S, Patel NR, Rodriguez-Granillo A, Robaire SA, Sherer EC, Truppo MD, Whittaker AM, Verma D, Xiao L, Xu Y, Yang H. Science 2019; 366: 1255
  • 20 Özgen FF, Runda ME, Schmidt S. ChemBioChem 2021; 22: 790
  • 21 Peñafiel I, Dryfe RA. W, Turner NJ, Greaney MF. ChemCatChem 2021; 13: 864