Chiral phosphoric acid-catalyzed enantioselective phosphinylation of 3,4-dihydroisoquinolines with diarylphosphine oxides.
Journal
Communications chemistry
ISSN: 2399-3669
Titre abrégé: Commun Chem
Pays: England
ID NLM: 101725670
Informations de publication
Date de publication:
09 Feb 2023
09 Feb 2023
Historique:
received:
29
09
2022
accepted:
31
01
2023
entrez:
9
2
2023
pubmed:
10
2
2023
medline:
10
2
2023
Statut:
epublish
Résumé
Chiral phosphorous-containing compounds are playing a more and more significant role in several different research fields. Here, we show a chiral phosphoric acid-catalyzed enantioselective phosphinylation of 3,4-dihydroisoquinolines with diarylphosphine oxides for the efficient and practical construction of a family of chiral α-amino diarylphosphine oxides with a diverse range of functional groups. The phosphine products are suitable for transforming to several kinds of chiral (thio)ureas, which might be employed as chiral ligands or catalysts with potential applications in asymmetric catalysis. Control and NMR tracking experiments show that the reaction proceeds via the tert-butyl 1-(tert-butoxy)-3,4-dihydroiso-quinoline-2(1H)-carboxylate intermediate, followed by C-P bond formation. Furthermore, computational studies elucidated that the hydrogen bonding strength between the phosphonate and isoquinolinium determines the stereoselectivity of the phosphinylation reaction.
Identifiants
pubmed: 36759563
doi: 10.1038/s42004-023-00826-4
pii: 10.1038/s42004-023-00826-4
pmc: PMC9911717
doi:
Types de publication
Journal Article
Langues
eng
Pagination
26Informations de copyright
© 2023. The Author(s).
Références
Tang, W.-J. & Zhang, X.-M. New chiral phosphorus ligands for enantioselective hydrogenation. Chem. Rev. 103, 3029–3070 (2003).
doi: 10.1021/cr020049i
pubmed: 12914491
Hayashi, T. Chiral monodentate phosphine ligand MOP for transition-metal-catalyzed asymmetric reactions. Acc. Chem. Res. 33, 354–362 (2000).
doi: 10.1021/ar990080f
pubmed: 10891053
Ni, H., Chan, W.-L. A. & Lu, Y. Phosphine-catalyzed asymmetric organic reactions. Chem. Rev. 118, 9344–9411 (2018).
doi: 10.1021/acs.chemrev.8b00261
pubmed: 30204423
Wan, F. A. & Tang, W.-J. Phosphorus ligands from the Zhang lab: Design, asymmetric hydrogenation, and industrial applications. Chin. J. Chem. 39, 954–968 (2021).
doi: 10.1002/cjoc.202000605
Carmona, J. A., Rodríguez-Franco, C., Fernández, R., Hornillos, V. & Lassaletta, J. M. Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies. Chem. Soc. Rev. 50, 2968–2983 (2021).
doi: 10.1039/D0CS00870B
pubmed: 33491680
Liu, L. et al. Copper-Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp3)−H/C(sp)−H Cross-Coupling with Rationally Designed Oxazoline-Derived N,N,P(O)-Ligands. Angew. Chem. Int. Ed. 133, 26914–26717 (2021).
doi: 10.1002/ange.202110233
Engel, R. Phosphonates as analogues of natural phosphates. Chem. Rev. 77, 349–367 (1977).
doi: 10.1021/cr60307a003
Romanenko, V. D. & Kukhar, V. P. Fluorinated phosphonates: Synthesis and biomedical application. Chem. Rev. 106, 3868–3935 (2006).
doi: 10.1021/cr051000q
pubmed: 16967924
Galezowska, J. & Gumienna-Kontecka, E. Phosphonates, their complexes and bio-applications: A spectrum of surprising diversity. Coord. Chem. Rev. 256, 105–124 (2012).
doi: 10.1016/j.ccr.2011.07.002
Horsman, G. P. & Zechel, D. L. Phosphonate biochemistry. Chem. Rev. 117, 5704–5783 (2017).
doi: 10.1021/acs.chemrev.6b00536
pubmed: 27787975
Parkinson, E. I., Erb, A., Eliot, A. C., Ju, K.-S. & Metcalf, W. W. Fosmidomycin biosynthesis diverges from related phosphonate natural products. Nat. Chem. Biol. 15, 1049–1056 (2019).
doi: 10.1038/s41589-019-0343-1
pubmed: 31451762
pmcid: 7098449
Baumgartner, T. & Réau, R. Organophosphorus π-conjugated materials. Chem. Rev. 106, 4681–4727 (2006).
doi: 10.1021/cr040179m
pubmed: 17091932
Mallesham, G. et al. Phosphine oxide functionalized pyrenes as efficient blue light emitting multifunctional materials for organic light emitting diodes. J. Mater. Chem. C. 3, 1208 (2015).
doi: 10.1039/C4TC01753F
Zhang, S.-A. et al. Highly efficient removal of uranium from highly acidic media achieved using a phosphine oxide and amino functionalized superparamagnetic composite polymer adsorbent. J. Mater. Chem. 8, 10925–10934 (2020).
doi: 10.1039/D0TA01633K
Liu, X.-W. et al. An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions. Org. Biomol. Chem. 6, 3997–4003 (2008).
doi: 10.1039/b811581h
pubmed: 18931808
Morris, D. J. et al. Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1, 2-diphenylethane-1, 2-diamine (PODPEN). Tetrahedron Lett. 51, 209–212 (2010).
doi: 10.1016/j.tetlet.2009.10.131
Turkbey, B., Hoyt, R. F., Agarwal, H. K., Bernardo, M. & Sankineni, S. Magnetic resonance sentinel lymph node imaging of the prostate with gadofosveset trisodium–albumin: Preliminary Results in a Canine Model. Acad. Radiol. 22, 646–652 (2015).
doi: 10.1016/j.acra.2014.12.021
pubmed: 25683498
pmcid: 4395526
Reddy, K. R. et al. Pradefovir: a prodrug that targets adefovir to the liver for the treatment of hepatitis B. J. Med. Chem. 51, 666–676 (2008).
doi: 10.1021/jm7012216
pubmed: 18173234
Lane, J. W., Chen, Y.-Y. & Williams, R. M. Asymmetric Total Syntheses of (−)-Jorumycin, (−)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G. J. Am. Chem. Soc. 127, 12684–12690 (2005).
doi: 10.1021/ja0535918
pubmed: 16144418
Vincent, G. & Williams, R. M. Asymmetric Total Synthesis of (−)‐Cribrostatin 4 (Renieramycin H). Angew. Chem. Int. Ed. 46, 1517 (2007).
doi: 10.1002/anie.200604126
Zhu, R.-H. et al. Chin. J. Chem. 32, 1039–1542 (2014).
doi: 10.1002/cjoc.201400471
Chrzanowska, M., Grajewska, A. & Rozwadowska, M. D. Asymmetric synthesis of isoquinoline alkaloids: 2004–2015. Chem. Rev. 116, 12369–12465 (2016).
doi: 10.1021/acs.chemrev.6b00315
pubmed: 27680197
Crestey, F. et al. Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists. J. Med. Chem. 56, 9673 (2013).
doi: 10.1021/jm4013592
pubmed: 24187998
Vitaku, E., Smith, D. T. & Njardarson, J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among US FDA approved pharmaceuticals: miniperspective. J. Med. Chem. 57, 10257–10274 (2014).
doi: 10.1021/jm501100b
pubmed: 25255204
Zhang, X.-L. et al. Structure-aided identification and optimization of tetrahydro-isoquinolines as novel PDE4 inhibitors leading to discovery of an effective antipsoriasis agent. J. Med. Chem. 62, 5579–5593 (2019).
doi: 10.1021/acs.jmedchem.9b00518
pubmed: 31099559
Sharma, U. K., Ranjan, P., Eycken, E. V. & You, S.-L. Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies. Chem. Soc. Rev. 49, 8721–8748 (2020).
doi: 10.1039/D0CS00128G
pubmed: 33079105
Chakka, S. K., Andersson, G., Maguire, G. E. M., Kruger, H. G. & Govender, T. Synthesis and Screening of C1‐Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions. Eur. J. Org. Chem. 5, 972–980 (2010).
doi: 10.1002/ejoc.200901159
Peters, B. et al. Novel tetrahydroisoquinoline based organocatalysts for asymmetric Diels–Alder reactions: insight into the catalytic mode using ROESY NMR and DFT studies. Tetrahedron.: Asymmetry. 21, 2859 (2010).
doi: 10.1016/j.tetasy.2010.11.010
Naicker, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. Tetrahydroisoquinoline‐Based N‐Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes. Eur. J. Org. Chem. 34, 6923 (2011).
doi: 10.1002/ejoc.201100923
Kawthekar, R. B. et al. Synthesis of tetrahydroisoquinoline (TIQ)–oxazoline ligands and their application in enantioselective Henry reactions. Tetrahedron.: Asymmetry. 21, 846 (2010).
doi: 10.1016/j.tetasy.2010.04.053
Cele, Z. E. D. et al. Catalytic asymmetric carbon–carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N, N′-dioxide ligands. Tetrahedron.: Asymmetry. 24, 191–195 (2013).
doi: 10.1016/j.tetasy.2013.01.004
Liu, W.-S., Liu, S.-S., Jin, R.-W., Guo, H. & Zhao, J.-B. Novel strategies for catalytic asymmetric synthesis of C1-chiral 1, 2, 3, 4-tetrahydroisoquinolines and 3, 4-dihydrotetrahydroisoquinolines. Org. Chem. Front. 2, 288–299 (2015).
doi: 10.1039/C4QO00294F
Yamakoshi, K., Harwood, S. J., Kanai, M. & Shibasaki, M. Catalytic asymmetric addition of diphenylphosphine oxide to cyclic imines. Tetrahedron Lett. 40, 2565–2568 (1999).
doi: 10.1016/S0040-4039(99)00203-8
Ingle, G. K. et al. Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides. Org. Lett. 13, 2054–2057 (2011).
doi: 10.1021/ol200456y
pubmed: 21413695
pmcid: 3115557
Kong, L.-P. et al. Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst. Org. Biomol. Chem. 12, 8656–8670 (2014).
doi: 10.1039/C4OB01472C
pubmed: 25252601
Ray, C. A. & Mukherjee, S. Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates. Chem. Sci. 7, 6940–6945 (2016).
doi: 10.1039/C6SC02466A
Gao, Z. & Guo, Y. Enantioselective phosphonation of isoquinolines via chiral phosphoric acid-catalyzed dearomatization. Chem. Commun. 58, 9393–9396 (2022).
doi: 10.1039/D2CC02811E
Akiyama, T., Itoh, J., Yokota, K. & Fuchibe, K. Enantioselective Mannich‐type reaction catalyzed by a chiral Brønsted acid. Angew. Chem. Int. Ed. 43, 1566–1594 (2004).
doi: 10.1002/anie.200353240
Uraguchi, D. & Terada, M. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. J. Am. Chem. Soc. 126, 5356–5357 (2004).
doi: 10.1021/ja0491533
pubmed: 15113196
Xu, F. et al. SPINOL-derived phosphoric acids: synthesis and application in enantioselective Friedel−Crafts reaction of indoles with imines. J. Org. Chem. 75, 8677–8680 (2010).
doi: 10.1021/jo101640z
pubmed: 21082787
Wang, L., Zhong, J. & Lin, X. Atroposelective Phosphoric Acid Catalyzed Three‐Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N‐Arylindoles. Angew. Chem. Int. Ed. 44, 15824–15828 (2019).
doi: 10.1002/anie.201909855
Akiyama, T. Stronger brønsted acids. Chem. Rev. 107, 5744–5758 (2007).
doi: 10.1021/cr068374j
pubmed: 17983247
Parmar, D., Sugiono, E., Raja, S. & Rueping, M. Complete Field Guide to Asymmetric BINOL Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates. Chem. Rev. 114, 9047–9153 (2014).
doi: 10.1021/cr5001496
pubmed: 25203602
Lin, X., Wang, L., Han, Z. & Chen, Z. Chiral spirocyclic phosphoric acids and their growing applications. Chin. J. Chem. 39, 802–824 (2021).
doi: 10.1002/cjoc.202000446
Guo, Y. et al. Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by a Chiral Phosphoric Acid: A Key Step in the Synthesis of the Bicyclic Guanidine Core of Crambescin A and Batzelladine A. Synthesis. 12, 2394–2406 (2018).
doi: 10.1055/s-0036-1591567
Guo, Y. et al. Chiral Spirocyclic Phosphoric Acid-Catalyzed Synthesis of 4-Alkyl-3,4-dihydropyrimidin-2(1H)-one Derivatives by Asymmetric Biginelli Reactions. Asian J. Org. Chem. 9, 626–630 (2020).
doi: 10.1002/ajoc.201900718
Guo, Y. et al. Practical catalytic enantioselective synthesis of 2, 3-dihydroquin-azolinones by chiral brønsted acid catalysis. Org. Biomol. Chem. 19, 4146–4151 (2021).
doi: 10.1039/D1OB00070E
pubmed: 33881128
Laconsay, C. J., Seguin, T. J. & Wheeler, S. E. Modulating Stereoselectivity through Electrostatic Interactions in a SPINOL-Phosphoric Acid-Catalyzed Synthesis of 2, 3-Dihydroquinazolinones. ACS Catal. 10, 12292–12299 (2020).
doi: 10.1021/acscatal.0c02578
Sasamoto, N., Dubs, C., Hamashima, Y. & Sodeoka, M. Pd (II)-catalyzed asymmetric addition of malonates to dihydroisoquinolines. J. Am. Chem. Soc. 128, 14010–14011 (2006).
doi: 10.1021/ja065646r
pubmed: 17061867
Michael, J., Rishel, M. J., Amarasinghe, K. K. D., Dinn, S. R. & Johnson, B. F. Asymmetric synthesis of tetrabenazine and dihydrotetrabenazine. J. Org. Chem. 74, 4001–4004 (2009).
doi: 10.1021/jo900480n
Zhang, M. et al. Enantioselective dearomative arylation of Isoquinolines. ACS Catal. 6, 5290–5294 (2016).
doi: 10.1021/acscatal.6b01693