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Synthesis 2019; 51(18): 3397-3409
DOI: 10.1055/s-0037-1611891
DOI: 10.1055/s-0037-1611891
short review
Synthesis of Phosphaproline Derivatives: A Short Overview
The work was supported by a grant from the President of the Russian Federation for support of young Russian scientists (MD-585.2019.3).Further Information
Publication History
Received: 23 May 2019
Accepted after revision: 25 June 2019
Publication Date:
15 July 2019 (online)
Abstract
Pyrrolidine-based phosphonates, analogues of the natural amino acid proline, possess a diverse set of biological activity. The goal of this short review is to summarize the major developments in the synthesis of phosphaproline derivatives reported since 2004 with special emphasis on the mechanisms and limitations of the methods presented.
1 Introduction
2 Phosphorylation of Pyrrolidine Derivatives
2.1 Syntheses via Pudovik Reaction
2.2 Syntheses via Arbuzov Reaction
2.3 Decarboxylative Phosphorylation of Proline
2.4 Direct C–H Bond Phosphorylation
2.5 Other Reactions
2.6 Overview of Phosphorylation Methods
3 Synthesis of 2-Phosphorylpyrrolidines from Acyclic Precursors
3.1 Cyclization of 4-Substituted Butylamine Derivatives
3.2 [3+2]-Dipolar Cycloaddition of α-Iminophosphonates
3.3 Cyclization of Aminoalkynes and 4-Aminocarbonyl Compounds
4 Conclusions
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References
- 1 Berlinck RG. S, Kossuga MH. Modern Alkaloids . Fattorusso E, Taglialatela-Scafati O. Wiley-VCH; Weinheim: 2007: 305-337
- 2 Dictionary of Alkaloids . Buckingham J, Baggaley KH, Roberts AD, Szabo LF. CRC Press; Boca Raton: 2010
- 3 Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 4 Gazizov AS, Smolobochkin AV, Anikina EA, Strelnik AG, Burilov AR, Pudovik MA. Synlett 2018; 29: 467
- 5 Smolobochkin AV, Gazizov AS, Burilov AR, Pudovik MA. Chem. Heterocycl. Compd. 2016; 52: 753
- 6 Upadhyay P, Kumar P. Synthesis 2010; 3063
- 7 Moonen K, Laureyn I, Stevens CV. Chem. Rev. 2004; 104: 6177
- 8 Mucha A, Kafarski P, Berlicki Ł. J. Med. Chem. 2011; 54: 5955
- 9 Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010; 17: 264
- 10 Sirrenberg W, Hammann I, Homeyer B. US 3911058, 1975
- 11 Sirrenberg W, Hammann I. US 3856892, 1999
- 12 Hassan J. US 6812224, 2004
- 13 Bugianesi LR, Doherty GA, Gentry A, Hale JJ, Lynch CL, Mills SG, Neway WE. III. US 7479504, 2009
- 14 Van der Veken P, Soroka A, Brandt I, Chen Y.-S, Maes M.-B, Lambeir A.-M, Chen X, Haemers A, Scharpé S, Augustyns K, De Meester I. J. Med. Chem. 2007; 50: 5568
- 15 Belyaev A, Zhang X, Augustyns K, Lambeir A.-M, De Meester I, Vedernikova I, Scharpé S, Haemers A. J. Med. Chem. 1999; 42: 1041
- 16 Gilmore BF, Carson L, McShane LL, Quinn D, Coulter WA, Walker B. Biochem. Biophys. Res. Commun. 2006; 347: 373
- 17 Sabidó E, Tarragó T, Niessen S, Cravatt BF, Giralt E. ChemBioChem 2009; 10: 2361
- 18 Camp NP, Hawkins PC. D, Hitchcock PB, Gani D. Bioorg. Med. Chem. Lett. 1992; 2: 1047
- 19 Camp NP, Perrey DA, Kinchington D, Hawkins PC. D, Gani D. Bioorg. Med. Chem. 1995; 3: 297
- 20 Iyer RP, Jin Y, Roland A. WO 03002587, 2003
- 21 Huang S, Chen Z, Du L, Tian Q, Liu Y, Zheng Y, Liu Y. Appl. Magn. Reson. 2015; 46: 489
- 22 Odinets I, Artyushin O, Shevchenko N, Petrovskii P, Nenajdenko V, Röschenthaler G.-V. Synthesis 2009; 577
- 23 Odinets IL, Artyushin OI, Lyssenko KA, Shevchenko NE, Nenajdenko VG, Röschenthaler G.-V. J. Fluorine Chem. 2009; 130: 662
- 24 Kamibayashi M, Oowada S, Kameda H, Okada T, Inanami O, Ohta S, Ozawa T, Makino K, Kotake Y. Free Radical Res. 2006; 40: 1166
- 25 Haak E, Bytschkov I, Doye S. Eur. J. Org. Chem. 2002; 2002: 457
- 26 Mao L.-L, Li C.-C, Yang Q, Cheng M.-X, Yang S.-D. Chem. Commun. 2017; 53: 4473
- 27 Mores A, Matziari M, Beau F, Cuniasse P, Yiotakis A, Dive V. J. Med. Chem. 2008; 51: 2216
- 28 Liu X.-W, Le TN, Lu Y, Xiao Y, Ma J, Li X. Org. Biomol. Chem. 2008; 6: 3997
- 29 Couture A, Deniau E, Lebrun S, Grandclaudon P, Carpentier J.-F. J. Chem. Soc., Perkin Trans. 1 1998; 1403
- 30 Borloo M, Jiao X.-Y, Wójtowicz H, Rajan P, Verbruggen C, Augustyns K, Haemers A. Synthesis 1995; 1074
- 31 Koeller KJ, Rath NP, Spilling CD. Phosphorus, Sulfur Silicon Relat. Elem. 1995; 103: 171
- 32 Arizpe A, Rodríguez-Mata M, Sayago FJ, Pueyo MJ, Gotor V, Jiménez AI, Gotor-Fernández V, Cativiela C. Tetrahedron: Asymmetry 2015; 26: 1469
- 33 Hirata S, Kuriyama M, Onomura O. Tetrahedron 2011; 67: 9411
- 34 Hanessian S, Gauchet C, Charron G, Marin J, Nakache P. J. Org. Chem. 2006; 71: 2760
- 35 Dondas HA, Durust Y, Grigg R, Slater MJ, Sarker MA. B. Tetrahedron 2005; 61: 10667
- 36 Baussanne I, Chiaroni A, Royer J. Tetrahedron: Asymmetry 2001; 12: 1219
- 37 Amedjkouh M, Westerlund K. Tetrahedron Lett. 2004; 45: 5175
- 38 Bhattacharya AK, Thyagarajan G. Chem. Rev. 1981; 81: 415
- 39 Chmielewska E, Miszczyk P, Kozłowska J, Prokopowicz M, Młynarz P, Kafarski P. J. Organomet. Chem. 2015; 785: 84
- 40 Romanenko VD, Kukhar VP. ARKIVOC 2012; (iv): 127
- 41 Chmielewska E, Kafarski P. Molecules 2016; 21: 1474
- 42 Boto A, Gallardo JA, Hernández R, Saavedra CJ. Tetrahedron Lett. 2005; 46: 7807
- 43 Hu J, Zhao N, Yang B, Wang G, Guo L.-N, Liang Y.-M, Yang S.-D. Chem. Eur. J. 2011; 17: 5516
- 44 Yang D, Zhao D, Mao L, Wang L, Wang R. J. Org. Chem. 2011; 76: 6426
- 45 Wu W.-B, Wong Y.-C, Tan Z.-K, Wu J. Catal. Sci. Technol. 2018; 8: 4257
- 46 Ho HE, Ishikawa Y, Asao N, Yamamoto Y, Jin T. Chem. Commun. 2015; 51: 12764
- 47 Han W, Mayer P, Ofial AR. Adv. Synth. Catal. 2010; 352: 1667
- 48 Das D, Seidel D. Org. Lett. 2013; 15: 4358
- 49 Kaname M, Arakawa Y, Yoshifuji S. Tetrahedron Lett. 2001; 42: 2713
- 50 Shevchenko N, Balenkova E, Röschenthaler G.-V, Nenajdenko V. Synthesis 2010; 120
- 51 Nenajdenko VG, Zakurdaev EP, Prusov EV, Balenkova ES. Tetrahedron 2004; 60: 11719
- 52 Gulevich AV, Shevchenko NE, Balenkova ES, Röschenthaler G.-V, Nenajdenko VG. Tetrahedron 2008; 64: 11706
- 53 Davis FA, Lee SH, Xu H. J. Org. Chem. 2004; 69: 3774
- 54 Li J.-S, Cui H.-F, Zhang K.-F, Nie J, Ma J.-A. Eur. J. Org. Chem. 2017; 2017: 2545
- 55 Qian R, Horak J, Hammerschmidt F. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 737
- 56 Ramírez-Marroquín OA, Romero-Estudillo II, Viveros-Ceballos JL. J. L, Cativiela C, Ordóñez M, Ramirez-Marroquin OA, Romero-Estudillo II, Viveros-Ceballos JL. J. L, Cativiela C, Ordonez M. Eur. J. Org. Chem. 2016; 2016: 308
- 57 Monbaliu J.-C, Tinant B, Marchand-Brynaert J. J. Org. Chem. 2010; 75: 5478
- 58 Davis FA, Bowen KA, Xu H, Velvadapu V. Tetrahedron 2008; 64: 4174
- 59 Davis FA, Wu Y, Xu H, Zhang J. Org. Lett. 2004; 6: 4523
- 60 Chen Q, Yuan C. Synthesis 2008; 1085
- 61 Taber DF, You KK, Rheingold AL. J. Am. Chem. Soc. 1996; 118: 547
- 62 Qian R, Kalina T, Horak J, Giberti S, Forlani G, Hammerschmidt F. ACS Omega 2018; 3: 4441
- 63 Wuggenig F, Schweifer A, Mereiter K, Hammerschmidt F. Eur. J. Org. Chem. 2011; 2011: 1870
- 64 Beck J, Gharbi S, Herteg-Fernea A, Vercheval L, Bebrone C, Lassaux P, Zervosen A, Marchand-Brynaert J. Eur. J. Org. Chem. 2009; 2009: 85
- 65 Matziari M, Bauer K, Dive V, Yiotakis A. J. Org. Chem. 2008; 73: 8591
- 66 Li G, Wu M, Liu F, Jiang J. Synthesis 2015; 47: 3783
- 67 Pursley D, Plietker B. Synlett 2014; 25: 2316
- 68 Robles-Machín R, González-Esguevillas M, Adrio J, Carretero JC. J. Org. Chem. 2010; 75: 233; highlighted in Synfacts 2010, 4, 0451
- 69 Cholakova T, Zagraniarsky Y, Simova S, Varbanov S, Dobrev A. Phosphorus, Sulfur Silicon Relat. Elem. 2005; 180: 1721
- 70 Yamashita Y, Guo X.-X, Takashita R, Kobayashi S. J. Am. Chem. Soc. 2010; 132: 3262
- 71 Yamashita Y, Nam LC, Dutton MJ, Yoshimoto S, Kobayashi S. Chem. Commun. 2015; 51: 17064
- 72 Han J, Paton R, Xu B, Hammond G. Synthesis 2013; 45: 463
- 73 Shioji K, Matsumoto A, Takao M, Kurauchi Y, Shigetomi T, Yokomori Y, Okuma K. Bull. Chem. Soc. Jpn. 2007; 80: 743
- 74 Dmitriev ME, Vinyukov AV, Lednev BV, Ragulin VV. Russ. J. Gen. Chem. 2017; 87: 2489
- 75 Vinyukov AV, Dmitriev ME, Yarkevich AN, Ragulin VV. Russ. J. Gen. Chem. 2017; 87: 2898
- 76 Vinyukov AV, Dmitriev ME, Afanas’ev AV, Ragulin VV, Andreeva LA, Myasoedov NF. Russ. J. Gen. Chem. 2017; 87: 266
- 77 Nasopoulou M, Georgiadis D, Matziari M, Dive V, Yiotakis A. J. Org. Chem. 2007; 72: 7222
- 78 Nenajdenko VG, Zakurdaev EP, Balenkova ES. Tetrahedron Lett. 2002; 43: 8449
- 79 Shmatova OI, Shevchenko NE, Balenkova ES, Röschenthaler G.-V, Nenajdenko VG. Eur. J. Org. Chem. 2013; 2013: 3049
- 80 Shmatova OI, Nenajdenko VG. Eur. J. Org. Chem. 2013; 2013: 6397
- 81 Shevchenko NE, Shmatova OI, Balenkova ES, Röschenthaler G.-V, Nenajdenko VG. Eur. J. Org. Chem. 2013; 2013: 2237