Asymmetric N-oxidation catalyzed by bisguanidinium dinuclear oxodiperoxomolybdosulfate

Kobus, M., Friedrich, T., Zorn, E., Burmeister, N. & Maison, W. Medicinal chemistry of drugs with N‑Oxide functionalities. J. Med. Chem. 67, 5168–5184 (2024).Article 
CAS 
PubMed 
PubMed Central 

Google Scholar 
Klein-Junior, L. C. et al. Targeted isolation of monoterpene indole alkaloids from Palicourea sessilis. J. Nat. Prod. 80, 3032–3037 (2017).Article 
CAS 
PubMed 

Google Scholar 
Bartolucci, C. et al. Structural determinants of torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819). J. Med. Chem. 49, 5051–5058 (2006).Article 
CAS 
PubMed 

Google Scholar 
Yeung, P. K. F., Mosher, S. J., Macrae, D. A. & Klassen, G. A. Effect of diltiazem and its metabolites on the uptake of adenosine in blood: an in-vitro investigation. J. Pharm. Pharmacol. 43, 685–689 (1991).Article 
CAS 
PubMed 

Google Scholar 
Liu, P. et al. New compound structure and preparation method and application thereof, Patent No. CN101885726A, (November, 17, 2010).Gao, W. et al. Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents. Bioorg. Med. Chem. Lett. 17, 4338–4342 (2007).Article 
CAS 
PubMed 

Google Scholar 
Tábi, T., Vécsei, L., Youdim, M. B., Riederer, P. & Szökő, É. Selegiline: A molecule with innovative potential. J. Neural Transm. 127, 831–842 (2020).Article 
PubMed 

Google Scholar 
Lévai, F. et al. In Vitro formation of selegiline-N-oxide as a metabolite of selegiline in human, hamster, mouse, rat, guinea-pig, rabbit and dog. Eur. J. Drug. Metab. Pharmacokinet. 29, 169–178 (2004).Article 
PubMed 

Google Scholar 
Liu, X. H., Lin, L. L. & Feng, X. M. Chiral N,N’-dioxides: new ligands and organocatalysts for catalytic asymmetric reactions. Acc. Chem. Res. 44, 574–587 (2011).Article 
CAS 
PubMed 

Google Scholar 
Malkov, A. V. & Kocovsky, P. Chiral N-oxides in asymmetric catalysis. Eur. J. Org. Chem. 1, 29–36 (2007).Article 

Google Scholar 
Chen, D. F., Gong, L. Z. & Feng, X. M. Chiral N.,N-dioxide ligands: uniqueness and impacts. Org. Chem. Front. 10, 3676–3683 (2023).Article 
CAS 

Google Scholar 
Traverse, J. F., Zhao, Y., Hoveyda, A. H. & Snapper, M. L. Proline-based N-oxides as readily available and modular chiral catalysts. enantioselective reactions of allyltrichlorosilane with aldehydes. Org. Lett. 7, 3151–3154 (2005).Article 
CAS 
PubMed 

Google Scholar 
Bickel, M. H. The Pharmacology and biology of N-oxides. Pharmacol. Rev. 21, 325–355 (1969).CAS 
PubMed 

Google Scholar 
Albini, A. Alkaloid N-oxides. Heterocycles 34, 1973–2002 (1992).Article 
CAS 

Google Scholar 
Lebar, M. D. et al. Identification and functional analysis of the aspergillic acid gene cluster in Aspergillus flavus. Fungal Genet. Biol. 116, 14–23 (2018).Article 
CAS 
PubMed 

Google Scholar 
Patterson, L. H. Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug. Metab. Rev. 34, 581–592 (2002).Article 
CAS 
PubMed 

Google Scholar 
O’Neil, I. Science of Synthesis, 40, 859–891 (Thieme 2009)Bernier, D., Wefelscheid, U. K. & Woodward, S. Properties, preparation and synthetic uses of amine N-oxides. an update. Org. Prep. Proced. Int. 41, 173–210 (2009).Article 
CAS 

Google Scholar 
Limnios, D. & Kokotos, C. G. 2,2,2-Trifluoroacetophenone as an organocatalyst for the oxidation of tertiary Amines and azines to N-Oxides. Chem. Eur. J. 20, 559–563 (2014).Article 
CAS 
PubMed 

Google Scholar 
Łukomska, M., Rybarczyk-Pirek, A. J., Jabłon´skib, M. & Palusiak, M. The nature of NO-bonding in N-oxide group. Phys. Chem. Chem. Phys. 17, 16375–16387 (2015).Article 
PubMed 

Google Scholar 
Baumeister, T. et al. Continuous flow synthesis of amine oxides by oxidation of tertiary amines. React. Chem. Eng. 4, 1270–1276 (2019).Article 
CAS 

Google Scholar 
Toda, F., Mori, K., Stein, Z. & Goldberg, I. Optical resolution of amine N-oxide by diastereoisomeric complex formation with optically active host compound. Tetrahedron Lett. 30, 1841–1844 (1989).Article 
CAS 

Google Scholar 
Drabowicz, J., Dudziński, B., Mikołajczyk, M., Colonna, S. & Gaggero, N. Chiral t-butylphenylphosphinothioic acid in NMR analysis of tertiary amine oxides with a stereogenic nitrogen atom. Tetrahedron. Asymmetry 8, 2267–2270 (1997).Article 
CAS 

Google Scholar 
Liu, W., Wang, D., Zhang, D. & Yang, X. Catalytic kinetic resolution and desymmetrization of amines. Synlett. 33, 1788–1812 (2022).Article 
CAS 

Google Scholar 
Wang, G., Lu, R., He, C. & Liu, L. Kinetic resolution of indolines by asymmetric hydroxylamine formation. Nat. Commun. 12, 2512 (2021).Article 
ADS 
CAS 
PubMed 
PubMed Central 

Google Scholar 
Colonna, S., Banfi, S. & Annunziata, R. Enantio- and diastereoselectivity in the periodate oxidation of sulfides catalyzed by bovine serum albumin. J. Org. Chem. 51, 891–895 (1986).Article 
CAS 

Google Scholar 
Colonna, S., Gaggero, N., Drabowicz, J., Łyżwa, P. & Mikolajczyk, M. The first efficient bovine serum albumin catalyzed asymmetric oxidation of tertiary amines to the corresponding N-oxides via kinetic dynamic resolution. Chem. Commun. 18, 1787–1788 (1999).Article 

Google Scholar 
Ottolina, G., Bianchi, S., Belloni, B., Carrea, G. & Danieli, B. First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase. Tetrahedron Lett. 40, 8483–8486 (1999).Article 
CAS 

Google Scholar 
Bergstad, K. & Baeckvall, J.-E. Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides. J. Org. Chem. 63, 6650–6655 (1998).Article 
CAS 

Google Scholar 
Zhang, S. et al. Biomimetic dynamic kinetic asymmetric N-oxidation with H2O2 and O2. ACS Catal. 13, 11954–11962 (2023).Article 
CAS 

Google Scholar 
Bhadra, S. & Yamamoto, H. Catalytic asymmetric synthesis of N-chiral amine oxides. Angew. Chem. Int. Ed. 55, 13043–13046 (2016).Article 
CAS 

Google Scholar 
Zong, L. & Tan, C.-H. Phase-transfer and ion-pairing catalysis of pentanidiums and bisguanidiniums. Acc. Chem. Res. 50, 842–856 (2017).Article 
CAS 
PubMed 

Google Scholar 
Ye, X. & Tan, C.-H. Enantioselective transition metal catalysis directed by chiral cations. Chem. Sci. 12, 533–539 (2021).Article 
CAS 

Google Scholar 
Wang, C., Zong, L. & Tan, C.-H. Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. J. Am. Chem. Soc. 137, 10677–10682 (2015).Article 
CAS 
PubMed 

Google Scholar 
Ye, X. et al. Enantioselective sulfoxidation catalyzed by a bisguanidinium diphosphatobisperoxotungstate ion pair. Angew. Chem. Int. Ed. 55, 7101–7105 (2016).Article 
CAS 

Google Scholar 
Zong, L. et al. Bisguanidinium dinuclear oxodiperoxomolybdosulfate ion-pair-catalyzed enantioselective sulfoxidation. Nat. Commun. 7, 13455–13464 (2016).Article 
ADS 
PubMed 
PubMed Central 

Google Scholar 
Chin, K. F. et al. Bisguanidinium-catalyzed epoxidation of allylic and homoallylic amines under phase transfer conditions. ACS Catal. 10, 2684–2691 (2020).Article 
CAS 

Google Scholar 
Bickelhaupt, F. M. & Houk, K. N. Analyzing reaction rates with the distortion/interaction-activation strain model. Angew. Chem. Int. Ed. 56, 10070–10086 (2017).Article 
CAS 

Google Scholar 

Hot Topics

Related Articles