Skip to main content
SpringerLink
Log in

Stereoselective Synthesis of Mono-fluoroalkenes

  • Chapter
  • First Online:
Stereoselective Alkene Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 327))

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Schlosser M (1978) Tetrahedron 34:3–17

    Article  CAS  Google Scholar 

  2. Welch JT (1987) Tetrahedron 43:3123–3197

    Article  CAS  Google Scholar 

  3. Pesenti C, Viani F (2004) Chem Bio Chem 5:590613

    Article  Google Scholar 

  4. Taguchi T, Yanai H (2009) In: Ojima I (ed) Fluorine in medicinal chemistry and chemical biology. Wiley, Chichester, pp 257–290

    Chapter  Google Scholar 

  5. Hara S (2005) In: Soloshonok VA (ed) Fluorine-containing synthons. American Chemical Society, Washington, pp 120–134

    Chapter  Google Scholar 

  6. Landelle G, Bergeron M, Savard MOT, Paquin JF (2011) Chem Soc Rev 40:2867–2908

    Article  CAS  Google Scholar 

  7. Yanai H, Taguchi T (2011) Eur J Org Chem 5939–5954

    Google Scholar 

  8. Olah GA, Welch JT, Vankar YD, Nojima M, Kerekes I, Olah JA (1979) J Org Chem 44:3872–3881

    Article  CAS  Google Scholar 

  9. Olah GA, Li X-Y(1990) Synlett 267–269

    Google Scholar 

  10. Albert P, Cousseau J (1985) Chem Commun 961–962

    Google Scholar 

  11. Gorgues A, Stéphan D, Cousseau J (1989) Chem Commun 1493–1494

    Google Scholar 

  12. Akana JA, Bhattacharyya KX, Müller P, Sadighi JP (2007) J Am Chem Soc 129:7734–7736

    Article  Google Scholar 

  13. Gorske BC, Mbofana CT, Miller SJ (2009) Org Lett 11:4318–4321

    Article  CAS  Google Scholar 

  14. Schuler M, Silva F, Bobbio C, Tessier A, Gouverneur V (2008) Angew Chem Int Ed 47:7927–7930

    Article  CAS  Google Scholar 

  15. Haro T, Nevado C (2011) Chem Commun 47:248–249

    Article  Google Scholar 

  16. Peng H, Liu G (2011) Org Lett 13:772–775

    Article  CAS  Google Scholar 

  17. Petasis NA, Yudin AK, Zavialov IA, Prakash GKS, Olah GA (1997) Synlett 606–608

    Google Scholar 

  18. Greedy B, Gouverneur V (2001) Chem Commun 233–234

    Google Scholar 

  19. Tius MA, Kawakami JK (1992) Synth Commun 22:1461–1471

    Article  CAS  Google Scholar 

  20. Tius MA, Kawakami JK (1993) Synlett 207–208

    Google Scholar 

  21. Tius MA, Kawakami JK (1995) Tetrahedron 51:3997–4010

    Article  CAS  Google Scholar 

  22. Lee SH, Schwartz J (1986) J Am Chem Soc 108:2445–2447

    Article  CAS  Google Scholar 

  23. Furuya T, Ritter T (2009) Org Lett 11:2860–2863

    Article  CAS  Google Scholar 

  24. Schlosser M, Zimmermann M (1969) Synthesis 75–76

    Google Scholar 

  25. Hayashi S, Nakai T, Ishikawa N, Burton DJ, Naae DG, Kesling HS (1979) Chem Lett 983–986

    Google Scholar 

  26. Grieco PA, Takigawa T, Vedananda TR (1985) J Org Chem 50:3111–3115

    Article  CAS  Google Scholar 

  27. Zhang X, Schlosser M (1993) Tetrahedron Lett 34:1925–1928

    Article  CAS  Google Scholar 

  28. Suzuki Y, Sato M (2004) Tetrahedron Lett 45:1679–1681

    Article  CAS  Google Scholar 

  29. Cox DG, Gurusamy N, Burton DJ (1985) J Am Chem Soc 107:2811–2821

    Article  CAS  Google Scholar 

  30. Burton DJ, Yang Z-Y, Qiu W (1996) Chem Rev 96:1641–1715

    Article  CAS  Google Scholar 

  31. Cincinelli R, Dallavalle S, Nannei R, Carella S, Zani DD, Merlini L, Penco S, Garattini E, Giannini G, Pisano C, Vesci L, Carminati P, Zuco V, Zanchi C, Zunino F (2005) J Med Chem 48:4931–4946

    Article  CAS  Google Scholar 

  32. Beaubien S, Deslongchamps P (2006) Can J Chem 84:29–48

    Article  CAS  Google Scholar 

  33. Lamy C, Hofmann J, Lopez HP, Goekjian P (2007) Tetrahedron Lett 48:6177–6180

    Article  CAS  Google Scholar 

  34. Sano S, Kuroda Y, Saito K, Ose Y, Nagao Y (2006) Tetrahedron 62:11881–11890

    Article  CAS  Google Scholar 

  35. Jakobsche CE, Peris G, Miller SJ (2008) Angew Chem Int Ed 47:6707–6711

    Article  CAS  Google Scholar 

  36. Noguchi T, Tanaka N, Nishimata T, Goto R, Hayakawa M, Sugidachi A, Ogawa T, Niitsu Y, Asai F, Ishizuka T, Fujimoto K (2009) Chem Pharm Bull 57:22–33

    Article  CAS  Google Scholar 

  37. Jakobsche CE, Choudhary A, Miller SJ, Raines RT (2010) J Am Chem Soc 132:6651–6653

    Article  CAS  Google Scholar 

  38. Zajc B, Kumar R (2010) Synthesis 1822–1836

    Google Scholar 

  39. Ghosh AK, Zajc B (2006) Org Lett 8:1553–1556

    Article  CAS  Google Scholar 

  40. Chevrie D, Lequeux T, Demoute JP, Pazenok S (2003) Tetrahedron Lett 44:8127–8130

    Article  CAS  Google Scholar 

  41. Pfund E, Lebargy C, Rouden J, Lequeux T (2007) J Org Chem 72:7871–7877

    Article  CAS  Google Scholar 

  42. Zajc B, Kake S (2006) Org Lett 8:4457–4460

    Article  CAS  Google Scholar 

  43. He M, Ghosh AK, Zajc B (2008) Synlett 999–1004

    Google Scholar 

  44. Solar M, Ghosh AK, Zajc B (2008) J Org Chem 73:8206–8211

    Article  Google Scholar 

  45. Ghosh AK, Banerjee S, Sinha S, Kang SB, Zajc B (2009) J Org Chem 74:3689–3697

    Article  CAS  Google Scholar 

  46. Zhang W, Huang W, Hu J (2009) Angew Chem Int Ed 48:9858–9861

    Article  CAS  Google Scholar 

  47. Urban JJ, Tillman BG, Cronin WA (2006) J Phys Chem A 110:11120–11129

    Article  CAS  Google Scholar 

  48. Bonnaire SC, Cahard D, Pannecoucke X (2007) Org Biomol Chem 5:1151–1157

    Article  Google Scholar 

  49. Otaka A, Watanabe H, Mitsuyama E, Yukimasa A, Tamamura H, Fujii N (2001) Tetrahedron Lett 42:285–287

    Article  CAS  Google Scholar 

  50. Otaka A, Watanabe H, Yukimasa A, Oishi S, Tamamura H, Fujii N (2001) Tetrahedron Lett 42:5443–5446

    Article  CAS  Google Scholar 

  51. Otaka A, Watanabe J, Yukimasa A, Sasaki Y, Watanabe H, Kinoshita T, Oishi S, Tamamura H, Fujii N (2004) J Org Chem 69:1634–1645

    Article  CAS  Google Scholar 

  52. Nakamura Y, Okada M, Koura M, Tojo M, Saito A, Sato A, Taguchi T (2006) J Fluor Chem 127:627–636

    Article  CAS  Google Scholar 

  53. Narumi T, Niida A, Tomita K, Oishi S, Otaka A, Ohno H, Fujii N (2006) Chem Commun 4720–4722

    Google Scholar 

  54. Narumi T, Tomita K, Inokuchi E, Kobayashi K, Oishi S, Ohno H, Fujii N (2008) Tetrahedron 64:4332–4346

    Article  CAS  Google Scholar 

  55. Oishi S, Kamitani H, Kodera Y, Watanabe K, Kobayashi K, Narumi T, Tomita K, Ohno H, Naito T, Kodama E, Matsuoka M, Fujii N (2009) Org Biomol Chem 7:2872–2877

    Article  CAS  Google Scholar 

  56. Narumi T, Hayashi R, Tomita K, Kobayashi K, Tanahara N, Ohno H, Naito T, Kodama E, Matsuoka M, Oishi S, Fujii N (2010) Org Biomol Chem 8:616–621

    Article  CAS  Google Scholar 

  57. Okada M, NakamuraY, Saito A, Sato A, Horikawa H, Taguchi T (2002) Chem Lett 28–29

    Google Scholar 

  58. Okada M, Nakamura Y, Saito A, Sato A, Horikawa H, Taguchi T (2002) Tetrahedron Lett 43:5845–5847

    Article  CAS  Google Scholar 

  59. Nakamura Y, Okada M, Sato A, Horikawa H, Koura M, Saito A, Taguchi T (2005) Tetrahedron 61:5741–5753

    Article  CAS  Google Scholar 

  60. Narumi T, Tomita K, Inokuchi E, Kobayashi K, Oishi S, Ohno H, Fujii N (2007) Org Lett 9:3465–3468

    Article  CAS  Google Scholar 

  61. Paquin J-F (2011) Synlett 289–293

    Google Scholar 

  62. Yamaki Y, Shigenaga A, Tomita K, Narumi T, Fujii N, Otaka A (2009) J Org Chem 74:3272–3277

    Article  CAS  Google Scholar 

  63. Yamaki Y, Shigenaga A, Li J, Shimohigashi Y, Otaka A (2009) J Org Chem 74:3278–3285

    Article  CAS  Google Scholar 

  64. Bejot R, Tisserand S, Reddy LM, Barma DK, Baati R, Falck JR, Mioskowski C (2005) Angew Chem Int Ed 44:2008–2011

    Article  CAS  Google Scholar 

  65. Nakagawa M, Saito A, Soga A, Yamamoto N, Taguchi T (2005) Tetrahedron Lett 46:5257–5261

    Article  CAS  Google Scholar 

  66. Zhang H, Zhou CB, Chen QY, Xiao JC, Hong R (2010) Org Lett 13:560–563

    Article  Google Scholar 

  67. Lei X, Dutheuil G, Pannecoucke X, Couve-Quirion J (2004) Org Lett 6:2101–2104

    Article  CAS  Google Scholar 

  68. Zoute L, Dutheuil G, Quirion JC, Jubault P, Pannecoucke X (2006) Synthesis 3409–3418

    Google Scholar 

  69. Xu J, Burton DJ (2005) J Org Chem 70:4346–4353

    Article  CAS  Google Scholar 

  70. Xu J, Burton DJ (2006) J Org Chem 71:3743–3747

    Article  CAS  Google Scholar 

  71. Andrei D, Wnuk SF (2006) J Org Chem 71:405–408

    Article  CAS  Google Scholar 

  72. Dutheuil G, Paturel C, Lei X, Bonnaire SC, Pannecoucke X (2006) J Org Chem 71:4316–4319

    Article  CAS  Google Scholar 

  73. Xu J, Burton DJ (2002) Org Lett 4:831–833

    Article  CAS  Google Scholar 

  74. McCarthy JR, Huber EW, Le TB, Laskovics FM, Matthews DP (1996) Tetrahedron 52:45–58

    Article  CAS  Google Scholar 

  75. Chen C, Wilcoxen K, Kim K, McCarthy JR (1997) Tetrahedron Lett 38:7677–7680

    Article  CAS  Google Scholar 

  76. Chen C, Wilcoxen K, Zhu YF, Kim K, McCarthy JR (1999) J Org Chem 64:3476–3482

    Article  CAS  Google Scholar 

  77. Saito A, Nakagawa M, Taguchi T (2005) J Fluor Chem 126:1166–1173

    Article  CAS  Google Scholar 

  78. Dutheuil G, Lei X, Pannecoucke X, Quirion JC (2005) J Org Chem 70:1911–1914

    Article  CAS  Google Scholar 

  79. Wang Z, Gonzalez A, Wnuk SF (2005) Tetrahedron Lett 46:5313–5316

    Article  CAS  Google Scholar 

  80. Dear REA (1970) J Org Chem 35:1703–1705

    Article  CAS  Google Scholar 

  81. Eddarir S, Mestdagh H, Rolando C (1991) Tetrahedron Lett 32:69–72

    Article  CAS  Google Scholar 

  82. Eddarir S, Francesch C, Mestdagh H, Rolando C (1997) Bull Soc Chim Fr 134:741–755

    CAS  Google Scholar 

  83. Williams DR, Fultz MW, Christos TE, Carter JS (2010) Tetrahedron Lett 51:121–124

    Article  CAS  Google Scholar 

  84. Hara S, Yoshida M, Fukuhara T, Yoneda N (1998) Chem Commun 965–966

    Google Scholar 

  85. Yoshida M, Kawakami K, Hara S (2004) Synthesis 2821–2824

    Google Scholar 

  86. Yoshida M, Hara S (2003) Org Lett 5:573–574

    Article  CAS  Google Scholar 

  87. Ochiai M, Oshima K, Masaki Y (1994) Chem Lett 871–874

    Google Scholar 

  88. Nguyen T, Abarbri M, Guilloteau D, Mavel S, Emond P (2011) Tetrahedron 67:3434–3439

    Article  CAS  Google Scholar 

  89. Yoshida M, Komata A, Hara S (2006) Tetrahedron 62:8636–8645

    Article  CAS  Google Scholar 

  90. Sakai M, Guan T, Hara S (2007) J Fluor Chem 128:1444–1448

    Article  CAS  Google Scholar 

  91. Yoshida M, Ota D, Fukuhara T, Yoneda N, Hara S (2002) J Chem Soc Perkin Trans 1 384–389

    Google Scholar 

  92. Guan T, Yoshida M, Ota D, Fukuhara T, Hara S (2005) J Fluor Chem 126:1185–1190

    Article  CAS  Google Scholar 

  93. Landelle G, Champagne PA, Barbeau X, Paquin JF (2009) Org Lett 11:681–684

    Article  CAS  Google Scholar 

  94. Stang PJ, Wingert H, Arif AM (1987) J Am Chem Soc 109:7235–7236

    Article  CAS  Google Scholar 

  95. Ochiai M, Kunishima M, Fuji K, Shiro M, Nagao Y (1988) Chem Commun 1076–1077

    Google Scholar 

  96. Ochiai M, Uemura K, Masaki Y (1993) J Am Chem Soc 115:2528–2529

    Article  CAS  Google Scholar 

  97. Guan T, Takemura K, Senboku H, Yoshida M, Hara S (2008) Tetrahedron Lett 49:76–79

    Article  CAS  Google Scholar 

  98. Hara S, Guan T, Yoshida M (2006) Org Lett 8:2639–2641

    Article  CAS  Google Scholar 

  99. Guan T, Yoshida M, Hara S (2007) J Org Chem 72:9617–9621

    Article  CAS  Google Scholar 

  100. Tranel F, Fröhlich R, Haufe G (2005) J Fluor Chem 126:557–569

    Article  CAS  Google Scholar 

  101. Wittmann, U, Tranel F, Fröhlich R, Haufe G (2006) Synthesis 2085–2096

    Google Scholar 

  102. Marhold M, Wittmann U, Grimme S, Takahashi T, Haufe G (2007) J Fluor Chem 128:1306–1317

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan

    Shoji Hara

Authors
  1. Shoji Hara
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shoji Hara .

Editor information

Editors and Affiliations

  1. , Department of Chemistry, Peking University, Beijing, 100871, China, People's Republic

    Jianbo Wang

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Hara, S. (2012). Stereoselective Synthesis of Mono-fluoroalkenes. In: Wang, J. (eds) Stereoselective Alkene Synthesis. Topics in Current Chemistry, vol 327. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2012_317

Download citation

Publish with us

Policies and ethics

Search

Navigation