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Synthesis 2025; 57(24): 3692-3698
DOI: 10.1055/a-2705-4396
DOI: 10.1055/a-2705-4396
Paper
Published as part of the Special Issue dedicated to Prof. Franziska Schoenebeck, recipient
of the 2025 Dr. Margaret Faul Women in Chemistry Award
Synthesis and Evaluation of Hydrogen-Bonding Organocatalysts Bearing P(V)-Stereogenic Centers
Authors
Supported by: China Scholarship Council and FAZIT-STIFTUNG
Abstract
In this study, we report the synthesis of a novel series of chiral hybrid scaffolds, each featuring a P(V)-stereogenic center integrated with a chiral backbone via squaramide or thiourea linkers. The catalytic performance of these newly developed organocatalysts was evaluated in asymmetric transfer hydrogenation reactions, showing moderate activity and limited selectivity.
Publication History
Received: 30 June 2025
Accepted after revision: 14 September 2025
Article published online:
09 October 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
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References
- 1a Ye X, Peng L, Bao X, Tan C-H, Wang H. Green Synth Catal 2021; 2: 6
- 1b Cui Y-M, Lin Y, Xu L-W. Coord Chem Rev 2017; 330: 37
- 1c Wei Y, Shi M. Acc Chem Res 2010; 43: 1005
- 2 Du Z-J, Guan J, Wu G-J, Xu P, Gao L-X, Han F-S. J Am Chem Soc 2015; 137: 632
- 3 Kortmann F. Dynamic Crystallization Processes of P-Chiral Phosphine Oxides. University of Groningen; 2014
- 4 Ferry A, Stemper J, Marinetti A, Voituriez A, Guinchard X. Eur J Org Chem 2014; 2014: 188
- 5 Huang Z, Huang X, Li B. et al. J Am Chem Soc 2016; 138: 7524
- 6 Qin X-L, Li A, Han F-S. J Am Chem Soc 2021; 143: 2994
- 7 Han ZS, Wu H, Qu B. et al. Tetrahedron Lett 1834; 2019: 60
- 8 Winters KR, Montchamp J-L. Beilstein J Org Chem 2022; 18: 1471
- 9a Von Leeuwen P. Supramolecular Catalysis. John Wiley & Sons; 2008
- 9b DiRocco DA, Ji Y, Sherer EC. et al. Science 2017; 356: 426
- 9c Devaki Venugopal H, Annadate RA, Pansare SVACS. Omega 2023; 8: 3190
- 10 Sohtome Y, Nagasawa K. Chem Commun 2012; 48: 7777
- 11a Rouf A, Tanyeli C. Curr Org Chem 2016; 20: 2996
- 11b Zhao BL, Li JH, Du DM. Chem Rec 2017; 17: 994
- 12 Dai L, Wang S-X, Chen F-E. Adv Synth Catal 2010; 352: 2137
- 13a Han ZS, Zhang L, Xu Y. et al. Angew Chem Int Ed 2015; 54: 5474
- 13b Han ZS, Wu H, Xu Y. et al. Org Lett 2017; 19: 1796
- 14 CCDC 2437879 (Rp-3), CCDC 2419212 (Rp-4a) and CCDC 2439956 (9b), contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre
- 15 Van Leeuwen PW. Supramolecular Catalysis. John Wiley & Sons; 2008
- 16 Sigman MS, Jacobsen EN. J Am Chem Soc 1998; 120: 4901
- 17 Hrishikesh DV, Annadate RA, Pansare SV. ACS Omega 2023; 8: 3190
- 18 Xu Q, Zhao C-Q, Han L-B. J Am Chem Soc 2008; 130: 12648
- 19 Zhou Y, Wang G, Saga Y. et al. J Org Chem 2010; 75: 7924
- 20 Tan KL, Jacobsen EN. Angew Chem Int Ed 2007; 46: 1315
- 21 Crépy KV, Imamoto T. Top Curr Chem 2003; 1
- 22 Qiao X, Bao Z, Xing H, Yang Y, Ren Q, Zhang Z. Catal Lett 2017; 147: 1673
- 23a Hasegawa A, Naganawa Y, Fushimi M, Ishihara K, Yamamoto H. Org Lett 2006; 8: 3175
- 23b Wenzel AG, Jacobsen EN. J Am Chem Soc 2002; 124: 12964
- 24 Xu Q, Zhao C-Q, Han L-B. J Am Chem Soc 2008; 130: 12648
- 25 Xu H, Zhang H, Jacobsen EN. Nat Protoc 1860; 2014: 9
- 26 Peng B, Ma J, Guo J. et al. J Am Chem Soc 2022; 144: 2853
- 27 A preprint of this work has been published: Wang Z, Christmann M. ChemRxiv 2025