Banert, K. et al.: 2019 Science of Synthesis: Knowledge Updates 2018/4 DOI: 10.1055/sos-SD-133-00040
Knowledge Updates 2018/4

33.1.1.2 Alk-1-enesulfonic Acids and Derivatives (Update 2018)

More Information

Book

Editors: Banert, K.; Clarke, P. A.; Drabowicz, J.; Oestreich, M.

Authors: Benoit, E.; Bull, J. A.; Croft, R. A.; Gagnon, A.; Kawęcki, R.; Kleoff, M.; Le Roch, A.; Omoregbee, K.; Podlech, J.; Zimmer, R.

Title: Knowledge Updates 2018/4

Print ISBN: 9783132423251; Online ISBN: 9783132423282; Book DOI: 10.1055/b-006-161209

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

 

Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods for the preparation of alk-1-enesulfonic acids and derivatives and their application in synthesis. This update focuses on methods published since 2004.

 
  • 1 Liu S, Zhou B, Yang H, He Y, Jiang Z.-X, Kumar S, Wu L, Zhang Z.-Y. J. Am. Chem. Soc 2008; 130: 8251
  • 2 Reddick J. J, Cheng J. M, Roush W. R. Org. Lett 2003; 5: 1967
  • 3 Badoni R, Semwal D. K, Rawat U, Singh G. J. P. Nat. Prod. Res 2010; 24: 1282
  • 4 Reck F, Zhou F, Girardot M, Kern G, Eyermann C. J, Hales N. J, Ramsay R. R, Gravestock M. B. J. Med. Chem 2005; 48: 499
  • 5 Moriarty R. M, Tyagi S. Org. Lett 2010; 12: 364
  • 6 Zilaout H, van den Hoogenband A, de Vries J, Lange J. H. M, Terpstra J. W. Tetrahedron Lett 2011; 52: 5934
  • 7 Gu Z, Zakarian A. Org. Lett 2011; 13: 1080
  • 8 Grandane A, Belyakov S, Trapencieris P, Zalubovskis R. Tetrahedron 2012; 68: 5541
  • 9 Tars K, Vullo D, Kazaks A, Leitans J, Lends A, Grandane A, Zalubovskis R, Scozzafava A, Supuran C. T. J. Med. Chem 2013; 56: 293
  • 10 Ghandi M, Bozcheloei A. H, Nazari S. H, Sadeghzadeh M. J. Org. Chem 2011; 76: 9975
  • 11 van Ameijde J, Slot T. K, Liskamp R. M. J. Tetrahedron: Asymmetry 2010; 21: 469
  • 12 Choi-Sledeski Y. M, Kearney R, Poli G, Pauls H, Gardner C, Gong Y, Becker M, Davis R, Spada A, Liang G, Chu V, Brown K, Collussi D, Leadley R, Rebello S, Moxey P, Morgan S, Bentley R, Kasiewski C, Maignan S, Guilloteau J. P, Mikol V. J. Med. Chem 2003; 46: 681
  • 13 Metaferia B. B, Fetterolf B. J, Shazad-ul-Hussan S, Moravec M, Smith J. A, Ray S, Gutierrez-Lugo M.-T, Bewley C. A. J. Med. Chem 2007; 50: 6326
  • 14 Jeanjean A, Gary-Bobo M, Nirdé P, Leiris S, Garcia M, Morére A. Bioorg. Med. Chem. Lett 2008; 18: 6240
  • 15 Herczeg M, Lazar L, Bereczky Z, Koever K. E, Timari I, Kappelmayer J, Liptak A, Antus S, Borbas A. Chem.–Eur. J 2012; 18: 10 643
  • 16 Liu J, Jiang F, Jin Y, Zhang Y, Liu J, Liu W, Fu L. Eur. J. Med. Chem 2012; 57: 10
  • 17 Kikuchi H, Okazaki K, Sekiya M, Uryu Y, Ueda K, Katou Y, Kurata S, Oshima Y. Eur. J. Med. Chem 2011; 46: 1263
  • 18 Shenai B. R, Lee B. J, Alvarez-Hernandez A, Chong P. Y, Emal C. D, Neitz R. J, Roush W. R, Rosenthal P. J. Antimicrob. Agents Chemother 2003; 47: 154
  • 19 Dana D, De S, Rathod P, Davalos A. R, Novoa D. A, Paroly S, Torres V. M, Afzal N, Lankalapalli R. S, Rotenberg S. A, Chang E. J, Subramaniam G, Kumar S. Chem. Commun. (Cambridge) 2014; 50: 10 875
  • 20 Lasheen D. S, Ismail M. A. H, Abou El Ella D. A, Ismail N. S. M, Eid S, Vleck S, Glenn J. S, Watts A. G, Abouzid K. A. M. Bioorg. Med. Chem 2013; 21: 2742
  • 21 Walleser P, Brückner R. Eur. J. Org. Chem 2014; 3210
  • 22 Le Flohic A, Meyer C, Cossy J, Desmurs J. R, Galland J. C. Synlett 2003; 667
  • 23 Karsch S, Freitag D, Schwab P, Metz P. Synthesis 2004; 1696
  • 24 Meyer C, Le Flohic A, Cossy J. Tetrahedron 2006; 62: 9017
  • 25 Mondal S, Debnath S. Tetrahedron Lett 2014; 55: 1577
  • 26 García-Rubia A, Urones B, Gómez Arráyas R, Carretero J. C. Angew. Chem. Int. Ed 2011; 50: 10 927
  • 27 Lu Y, Wang D.-H, Engle K. M, Yu J.-Q. J. Am. Chem. Soc 2010; 132: 5916
  • 28 Huang C, Chattopadhyay B, Gevorgyan V. J. Am. Chem. Soc 2011; 133: 12 406
  • 29 Nardello V, Aubry J. M, Johnston P, Bulduk I, de Vries A. H. M, Alsters P. L. Synlett 2005; 2667
  • 30 Battace A, Zair T, Doucet H, Santelli M. Synthesis 2006; 3495
  • 31 Prakash G. K. S, Jog P. V, Krishnan H. S, Olah G. A. J. Am. Chem. Soc 2011; 133: 2140
  • 32 Marinozzi M, Fulco M. C, Amori L, Fiumi M, Pellicciari R. Tetrahedron 2009; 65: 7092
  • 33 Aramini A, Cesta M. C, Coniglio S, Bijani C, Colagioia S, D’Elia V, Allegretti M. J. Org. Chem 2003; 68: 7911
  • 34 Yamada M, Ichikawa T, Ii M, Sunamoto M, Itoh K, Tamura N, Kitazaki T. J. Med. Chem 2005; 48: 7457
  • 35 Enders D, Wallert S, Runsink J. Synthesis 2003; 1856
  • 36 Prishchenko A. A, Livantsov M. V, Novikova O. P, Livantsova L. I, Pol’shchikov D. G. Russ. J. Gen. Chem. (Engl. Transl.) 2004; 74: 1820
  • 37 Prishchenko A. A, Livantsov M. V, Novikova O. P, Livantsova L. I, Petrosyan V. S. Heteroat. Chem 2008; 19: 470
  • 38 Lu J, Ye J, Duan W.-L. Org. Lett 2013; 15: 5016
  • 39 Lu J, Ye J, Duan W.-L. Chem. Commun. (Cambridge) 2014; 50: 698
  • 40 García-Gallego S, Serrami M. J, Arnaiz E, Díaz L, Muñoz-Fernndez M. A, Gomez-Sal P, Ottaviani M. F, Gómez R, de la Mata F. J. Eur. J. Inorg. Chem 2011; 1657
  • 41 Winkel A, Wilhelm R. Eur. J. Org. Chem 2010; 5817
  • 42 Rasines B, Snchez-Nieves J, Maiolo M, Maly M, Chonco L, Jiménez J. L, Muñoz-Fernndez M. Á, de la Mata F. J, Gómez R. Dalton Trans 2012; 41: 12 733
  • 43 García-Gallego S, Cangiotti M, Fiorani L, Fattori A, Muñoz-Fernndez M. A, Gomez R, Ottaviani M. F, de la Mata F. J. Dalton Trans 2013; 42: 5874
  • 44 Chudasama V, Wilden J. D. Chem. Commun. (Cambridge) 2008; 3768
  • 45 Zhou A, Hanson P. R. Org. Lett 2008; 10: 2951
  • 46 Asad N, Samarakoon T. B, Zang Q, Loh J. K, Javed S, Hanson P. R. Org. Lett 2014; 16: 82
  • 47 Zhou A, Rayabarapu D, Hanson P. R. Org. Lett 2009; 11: 531
  • 48 Ji T, Wang Y, Wang M, Niu B, Xie P, Pittman Jr. C. U, Zhou A. ACS Comb. Sci 2013; 15: 595
  • 49 Edetanlen-Elliot O, Fitzmaurice R. J, Wilden J. D, Caddick S. Tetrahedron Lett 2007; 48: 8926
  • 50 Fitzmaurice R. J, Ahern J. M, Caddick S. Org. Biomol. Chem 2009; 7: 235
  • 51 Chudasama V, Fitzmaurice R. J, Ahern J. M, Caddick S. Chem. Commun. (Cambridge) 2010; 46: 133
  • 52 Chudasama V, Akhbar A. R, Bahou K. A, Fitzmaurice R. J, Caddick S. Org. Biomol. Chem 2013; 11: 7301
  • 53 Niu B, Xu L, Xie P, Wang M, Zhao W, Pittman Jr. C. U, Zhou A. ACS Comb. Sci 2014; 16: 454
  • 54 Zhao M. M, Qu C, Lynch J. E. J. Org. Chem 2005; 70: 6944
  • 55 Nishimura T, Takiguchi Y, Hayashi T. J. Am. Chem. Soc 2012; 134: 9086
  • 56 Caddick S, Bush H. D. Org. Lett 2003; 5: 2489
  • 57 Tian L, Xu G. Y, Liu L. Z. Synthesis 2003; 1329
  • 58 Ghandi M, Taheri A, Bozcheloei A. H, Abbasi A, Kia R. Tetrahedron 2012; 68: 3641
  • 59 Tian L, Xu G. Y, Ye Y, Liu L. Z. J. Heterocycl. Chem 2003; 40: 1071
  • 60 Lee C. C, Fitzmaurice R. J, Caddick S. Org. Biomol. Chem 2009; 7: 4349
  • 61 Shi B, Merten S, Wong D. K. Y, Chu J. C. K, Liu L. L, Lam S. K, Jäger A, Wong W.-T, Chiu P, Metz P. Adv. Synth. Catal 2009; 351: 3128
  • 62 Rogachev V. O, Metz P. Nat. Protoc 2006; 1: 3076
  • 63 Rogachev V. O, Filimonov V. D, Fröhlich R, Kataeva O, Metz P. Heterocycles 2006; 67: 589
  • 64 Rogachev V. O, Metz P. ARKIVOC 2007; 167
  • 65 Zhou H.-B, Comninos J. S, Stossi F, Katzenellenbogen B. S, Katzenellenbogen J. A. J. Med. Chem 2005; 48: 7261
  • 66 Wang P, Min J, Nwachukwu J. C, Cavett V, Carlson K. E, Guo P, Zhu M, Zheng Y, Dong C, Katzenellenbogen J. A, Nettles K. W, Zhou H.-B. J. Med. Chem 2012; 55: 2324
  • 67 Zheng Y, Wang C, Li C, Qiao J, Zhang F, Huang M, Ren W, Dong C, Huang J, Zhou H.-B. Org. Biomol. Chem 2012; 10: 9689
  • 68 Ghandi M, Mohammadimehr E, Sadeghzadeh M, Bozcheloei A. H. Tetrahedron 2011; 67: 8484
  • 69 Moghaddam F. M, Khodabakhshi M. R, Kiamehr M, Ghahremannejad Z. Tetrahedron Lett 2013; 54: 2685