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DOI: 10.1055/s-0043-1775441
Enantioselective Wittig Reactions Controlled by PIII/PV=O Redox Catalysis
This project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (grant agreement No. 101002471).
Abstract
The development of catalytic PIII/PV=O redox processes has transformed the Wittig reaction, traditionally plagued by stoichiometric phosphine oxide byproducts, into an efficient and more benign method for synthesizing alkenes. Recently, the feasibility of enantioselective PIII/PV=O redox catalysis was demonstrated by using chiral phosphine catalysts, such as HypPhos. For example, an atroposelective Wittig reaction using Boc-MBH adducts, where endogenous base release facilitates ylide formation and acid co-catalysis, allows enantiocontrol and effective PIII/PV=O redox cycling, while catalyst-stereocontrolled enantioselective Wittig reactions generally extend the scope and sustainability of the synthesis of complex molecules.
1 Introduction
2 meso-Desymmetrizations
3 Atroposelective Catalysis
4 Conclusion
Key words
Wittig reaction - stereoselectivity - redox catalysis - meso-desymmetrization - atropisomersPublikationsverlauf
Eingereicht: 30. Oktober 2024
Angenommen: 17. Dezember 2024
Artikel online veröffentlicht:
03. Februar 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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References
- 1 Wittig G, Schöllkopf U. Chem. Ber. 1954; 87: 1318
- 2 Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 3 Hoffmann RW. Angew. Chem. Int. Ed. 2001; 40: 1411
- 4 Byrne PA, Gilheany DG. Chem. Soc. Rev. 2013; 42: 6670
- 5 O’Brien CJ, Tellez JL, Nixon ZS, Kang LJ, Carter AL, Kunkel SR, Przeworski KC, Chass GA. Angew. Chem. Int. Ed. 2009; 48: 6836
- 6 O’Brien CJ, Nixon ZS, Holohan AJ, Kunkel SR, Tellez JL, Doonan BJ, Coyle EE, Lavigne F, Kang LJ, Przeworski KC. Chem. Eur. J. 2013; 19: 15281
- 7 Coyle EE, Doonan BJ, Holohan AJ, Walsh KA, Lavigne F, Krenske EH, O’Brien CJ. Angew. Chem. Int. Ed. 2014; 53: 12907
- 8 Lao Z, Toy PH. Beilstein J. Org. Chem. 2016; 12: 2577
- 9 Zhang K, Cai L, Yang Z, Houk KN, Kwon O. Chem. Sci. 2018; 9: 1867
- 10 Longwitz L, Spannenberg A, Werner T. ACS Catal. 2019; 9: 9237
- 11 Xie C, Smaligo AJ, Song X.-R, Kwon O. ACS Cent. Sci. 2021; 7: 536
- 12 Werner T, Hoffmann M, Deshmukh S. Eur. J. Org. Chem. 2014; 6630
- 13 Schneider LM, Schmiedel VM, Pecchioli T, Lentz D, Merten C, Christmann M. Org. Lett. 2017; 19: 2310
- 14 Schmiedel VM, Hong YJ, Lentz D, Tantillo DJ, Christmann M. Angew. Chem. Int. Ed. 2018; 57: 2419
- 15 Cai L, Zhang K, Chen S, Lepage RJ, Houk KN, Krenske EH, Kwon O. J. Am. Chem. Soc. 2019; 141: 9537
- 16 Yang H, Zhang J, Zhang S, Xue Z, Hu S, Chen Y, Tang Y. J. Am. Chem. Soc. 2024; 146: 14136
- 17 Xie C, Kim J, Mai BK, Cao S, Ye R, Wang X.-Y, Liu P, Kwon O. J. Am. Chem. Soc. 2022; 144: 21318
- 18 Moser D, Jana K, Sparr C. Angew. Chem. Int. Ed. 2023; 62: e202309053
- 19 Lorton C, Castanheiro T, Voituriez A. J. Am. Chem. Soc. 2019; 141: 10142
- 20 Link A, Sparr C. Angew. Chem. Int. Ed. 2014; 53: 5458
- 21 Lotter D, Neuburger M, Rickhaus M, Häussinger D, Sparr C. Angew. Chem. Int. Ed. 2016; 55: 2920
- 22 Witzig RM, Fäseke VC, Häussinger D, Sparr C. Nat. Catal. 2019; 2: 925
- 23 Jončev Z, Sparr C. Angew. Chem. Int. Ed. 2022; 61: e202211168
- 24 Xie P, Huang Y, Chen R. Chem. Eur. J. 2012; 18: 7362
- 25 Xie P, Huang Y. Org. Biomol. Chem. 2015; 13: 8578
- 26 Zhou R, He Z. Eur. J. Org. Chem. 2016; 1937
- 27 Ni H, Chan W.-L, Lu Y. Chem. Rev. 2018; 118: 9344
- 28 Jin H, Lai J, Huang Y. Org. Lett. 2019; 21: 2843
- 29 Lin J, Zhu Y, Cai W, Huang Y. Org. Lett. 2022; 24: 1593
- 30 Jana K, Zhao Z, Musies J, Sparr C. Angew. Chem. Int. Ed. 2024; 63: e202408159