Synthesis and Evaluation of Hydrogen-Bonding Organocatalysts Bearing P(V)-Stereogenic Centers

Zhen Wang; Nadine Kreidt; Mathias Christmann

doi:10.1055/a-2705-4396

Synthesis 2025; 57(24): 3692-3698
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

Zhen Wang

¹Biology, Chemistry, Pharmacy, FU Berlin, Berlin, Germany
Nadine Kreidt

¹Biology, Chemistry, Pharmacy, FU Berlin, Berlin, Germany
Mathias Christmann

¹Biology, Chemistry, Pharmacy, FU Berlin, Berlin, Germany

Abstract

All articles of this category

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.

Keywords

Phosphorus - Stereoselective synthesis - Squaramides - Thioureas - Organocatalysis

Full Text

References

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

Supplementary Material

Supplementary Material (PDF) (opens in new window)