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Stereoselective Synthesis of Z-Alkenes

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Stereoselective Alkene Synthesis

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

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References

  1. Knowles WS (2002) Angew Chem Int Ed 41:1998–2007

    Article  CAS  Google Scholar 

  2. Noyori R (2002) Angew Chem Int Ed 41:2008–2022

    Article  CAS  Google Scholar 

  3. Sharpless KB (2002) Angew Chem Int Ed 41:2024–2032

    Article  CAS  Google Scholar 

  4. Chauvin Y (2006) Angew Chem Int Ed 45:3740–3747

    Article  Google Scholar 

  5. Schrock RR (2006) Angew Chem Int Ed 45:3748–3759

    Article  CAS  Google Scholar 

  6. Grubbs RH (2006) Angew Chem Int Ed 45:3760–3765

    Article  CAS  Google Scholar 

  7. Vedejs E, Peterson MJ (1996) Adv Carbanion Chem 2:1–85

    Article  CAS  Google Scholar 

  8. Nicolaou KC, Harter MW, Gunzner JL, Nadin A (1997) Liebigs Ann/Recl 1283–1301

    Google Scholar 

  9. Murphy PJ, Lee SE (1999) J Chem Soc Perkin Trans 1 3049–3212

    Google Scholar 

  10. Rein T, Pedersen TM (2002) Synthesis 579–594

    Google Scholar 

  11. Smith AB III, Beauchamp TJ, LaMarche MJ, Kaufman MD, Qiu Y, Arimoto H, Jones DR, Kobayashi K (2000) J Am Chem Soc 122:8654–8664

    Article  CAS  Google Scholar 

  12. Stork G, Zhao K (1989) Tetrahedron Lett 30:2173–2174

    Article  CAS  Google Scholar 

  13. Chen J, Wang T, Zhao K (1994) Tetrahedron Lett 35:2827–2828

    Article  CAS  Google Scholar 

  14. Dong D-J, Li H-H, Tian S-K (2010) J Am Chem Soc 132:5018–5020

    Article  CAS  Google Scholar 

  15. O'Brien CJ, Tellez JL, Nixon ZS, Kang LJ, Carter AL, Kunkel SR, Przeworski KC, Chass GA (2009) Angew Chem Int Ed 48:6836–6839

    Article  Google Scholar 

  16. Minami T, Okauchi T, Kouno R (2001) Synthesis 349–357

    Google Scholar 

  17. Still WC, Gennari C (1983) Tetrahedron Lett 24:4405–4408

    Article  CAS  Google Scholar 

  18. Motoyoshiya J (1998) Trends Org Chem 7:63–73

    CAS  Google Scholar 

  19. Mergott DJ, Frank SA, Roush WR (2002) Org Lett 4:3157–3160

    Article  CAS  Google Scholar 

  20. Motoyoshiya J, Kusaura T, Kokin K, Yokoya Si, Takaguchi Y, Narita S, Aoyama H (2001) Tetrahedron 57:1715–1721

    Article  CAS  Google Scholar 

  21. E-i N, Huang Z, Wang G, Mohan S, Wang C, Hattori H (2008) Acc Chem Res 41:1474–1485

    Article  Google Scholar 

  22. Molander GA, Dehmel F (2004) J Am Chem Soc 126:10313–10318

    Article  CAS  Google Scholar 

  23. Huang Z, Negishi E-I (2007) J Am Chem Soc 129:14788–14792

    Article  CAS  Google Scholar 

  24. Belardi JK, Micalizio GC (2008) J Am Chem Soc 130:16870–16872

    Article  CAS  Google Scholar 

  25. Lindlar H, Dubuis R (1966) Org Synth 46:89–91

    CAS  Google Scholar 

  26. Ghosh AK, Wang Y, Kim JT (2001) J Org Chem 66:8973–8974

    Article  CAS  Google Scholar 

  27. Fuerstner A, Guth O, Rumbo A, Seidel G (1999) J Am Chem Soc 121:11108–11113

    Article  CAS  Google Scholar 

  28. Wengrovius JH, Sancho J, Schrock RR (1981) J Am Chem Soc 103:3932–3934

    Article  CAS  Google Scholar 

  29. Cummins CC (1998) Chem Commun (Cambridge) 1777–1786

    Google Scholar 

  30. Fuerstner A, Davies PW (2005) Chem Commun (Cambridge UK) 2307–2320

    Google Scholar 

  31. Gruttadauria M, Noto R, Deganello G, Liotta LF (1999) Tetrahedron Lett 40:2857–2858

    Article  CAS  Google Scholar 

  32. Gruttadauria M, Liotta LF, Noto R, Deganello G (2001) Tetrahedron Lett 42:2015–2017

    Article  CAS  Google Scholar 

  33. Brown CA, Ahuja VK (1973) J Chem Soc, Chem Commun 553–554

    Google Scholar 

  34. Oger C, Bultel-Ponce V, Guy A, Balas L, Rossi J-C, Durand T, Galano J-M (2010) Chem Eur J 16:13976–13980

    Article  CAS  Google Scholar 

  35. Harada K, Urabe H, Sato F (1995) Tetrahedron Lett 36:3203–3206

    Article  CAS  Google Scholar 

  36. Gianetti TL, Tomson NC, Arnold J, Bergman RG (2011) J Am Chem Soc 133:14904–14907

    Article  CAS  Google Scholar 

  37. Parenty A, Campagne J-M (2002) Tetrahedron Lett 43:1231–1233

    Article  CAS  Google Scholar 

  38. Sato F, Ishikawa H, Sato M (1981) Tetrahedron Lett 22:85–88

    Article  CAS  Google Scholar 

  39. Brown HC, Hamaoka T, Ravindran N (1973) J Am Chem Soc 95:6456–6457

    Article  CAS  Google Scholar 

  40. Ohmura T, Yamamoto Y, Miyaura N (2000) J Am Chem Soc 122:4990–4991

    Article  CAS  Google Scholar 

  41. Asao N, Liu J-X, Sudoh T, Yamamoto Y (1996) J Org Chem 61:4568–4571

    Article  CAS  Google Scholar 

  42. Na Y, Chang S (2000) Org Lett 2:1887–1889

    Article  CAS  Google Scholar 

  43. Takami K, Yorimitsu H, Oshima K (2002) Org Lett 4:2993–2995

    Article  CAS  Google Scholar 

  44. Schwier T, Gevorgyan V (2005) Org Lett 7:5191–5194

    Article  CAS  Google Scholar 

  45. Hoveyda AH, Zhugralin AR (2007) Nature (London UK) 450:243–251

    Article  CAS  Google Scholar 

  46. Randall ML, Tallarico JA, Snapper ML (1995) J Am Chem Soc 117:9610–9611

    Article  CAS  Google Scholar 

  47. Tallarico JA, Randall ML, Snapper ML (1997) Tetrahedron 53:16511–16520

    Article  CAS  Google Scholar 

  48. Crowe WE, Goldberg DR (1995) J Am Chem Soc 117:5162–5163

    Article  CAS  Google Scholar 

  49. Randl S, Gessler S, Wakamatsu H, Blechert S (2001) Synlett 430–432

    Google Scholar 

  50. Kang B, Kim D-H, Do Y, Chang S (2003) Org Lett 5:3041–3043

    Article  CAS  Google Scholar 

  51. Hansen EC, Lee D (2004) Org Lett 6:2035–2038

    Article  CAS  Google Scholar 

  52. Kang B, Lee JM, Kwak J, Lee YS, Chang S (2004) J Org Chem 69:7661–7664

    Article  CAS  Google Scholar 

  53. Sashuk V, Samojlowicz C, Szadkowska A, Grela K (2008) Chem Commun (Cambridge UK) 2468–2480

    Google Scholar 

  54. Xu Z, Johannes CW, Salman SS, Hoveyda AH (1996) J Am Chem Soc 118:10926–10927

    Article  CAS  Google Scholar 

  55. Llacer E, Urpi F, Vilarrasa J (2009) Org Lett 11:3198–3201

    Article  CAS  Google Scholar 

  56. Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH (2008) Nature (London UK) 456:933–937

    Article  CAS  Google Scholar 

  57. Sattely ES, Meek SJ, Malcolmson SJ, Schrock RR, Hoveyda AH (2009) J Am Chem Soc 131:943–953

    Article  CAS  Google Scholar 

  58. Ibrahem I, Yu M, Schrock RR, Hoveyda AH (2009) J Am Chem Soc 131:3844–3845

    Article  CAS  Google Scholar 

  59. Flook MM, Jiang AJ, Schrock RR, Muller P, Hoveyda AH (2009) J Am Chem Soc 131:7962–7963

    Article  CAS  Google Scholar 

  60. Flook MM, Ng VWL, Schrock RR (2011) J Am Chem Soc 133:1784–1786

    Article  CAS  Google Scholar 

  61. Jiang AJ, Zhao Y, Schrock RR, Hoveyda AH (2009) J Am Chem Soc 131:16630–16631

    Article  CAS  Google Scholar 

  62. Marinescu SC, Schrock RR, Muller P, Takase MK, Hoveyda AH (2011) Organometallics 30:1780–1782

    Article  CAS  Google Scholar 

  63. Meek SJ, O'Brien RV, Llaveria J, Schrock RR, Hoveyda AH (2011) Nature (London UK) 471:461–466

    Article  CAS  Google Scholar 

  64. Lee Y, Jang H, Hoveyda AH (2009) J Am Chem Soc 131:18234–18235

    Article  CAS  Google Scholar 

  65. Qin D, Byun H-S, Bittman R (1999) J Am Chem Soc 121:662–668

    Article  CAS  Google Scholar 

  66. Nicolaou KC, Winssinger N, Pastor J, Ninkovic S, Sarabia F, He Y, Vourloumis D, Yang Z, Li T, Giannakakou P, Hamel E (1997) Nature (London) 387:268–272

    Article  CAS  Google Scholar 

  67. Su D-S, Meng D, Bertinato P, Balog A, Sorensen EJ, Danishefsky SJ, Zheng Y-H, Chou T-C, He L, Horwitz SB (1997) Angew Chem Int Ed Engl 36:757–759

    Article  CAS  Google Scholar 

  68. Yu M, Wang C, Kyle AF, Jakubec P, Dixon DJ, Schrock RR, Hoveyda AH (2011) Nature 479:88–93

    Article  CAS  Google Scholar 

  69. Endo K, Grubbs RH (2011) J Am Chem Soc 133:8525–8527

    Article  CAS  Google Scholar 

  70. Keitz BK, Endo K, Herbert MB, Grubbs RH (2011) J Am Chem Soc 133:9686–9688

    Article  CAS  Google Scholar 

  71. Barbero A, Blanco Y, Garcia C, Pulido FJ (2000) Synthesis 1223–1228

    Google Scholar 

  72. Prantz K, Mulzer J (2009) Angew Chem Int Ed 48:5030–5033

    Article  CAS  Google Scholar 

  73. Su W, Jin C (2007) Org Lett 9:993–996

    Article  CAS  Google Scholar 

  74. Nonoshita K, Banno H, Maruoka K, Yamamoto H (1990) J Am Chem Soc 112:316–322

    Article  CAS  Google Scholar 

  75. Basavaiah D, Sarma PKS (1992) J Chem Soc, Chem Commun 955–957

    Google Scholar 

  76. Kabalka GW, Venkataiah B, Dong G (2003) Org Lett 5:3803–3805

    Article  CAS  Google Scholar 

  77. Yazaki R, Nitabaru T, Kumagai N, Shibasaki M (2008) J Am Chem Soc 130:14477–14479

    Article  CAS  Google Scholar 

  78. Yazaki R, Kumagai N, Shibasaki M (2009) J Am Chem Soc 131:3195–3197

    Article  CAS  Google Scholar 

  79. Yazaki R, Kumagai N, Shibasaki M (2010) J Am Chem Soc 132:5522–5531

    Article  CAS  Google Scholar 

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Acknowledgments

We are grateful to National University of Singapore and National Research Foundation of Singapore for their support of our research program.

Author information

Authors and Affiliations

  1. Department of Chemistry, National University of Singapore, Singapore, 117543, Singapore

    Woon-Yew Siau

  2. Department of Chemistry, National University of Singapore, Singapore, 117543, Singapore

    Yao Zhang

  3. Department of Chemistry, National University of Singapore, Singapore, 117543, Singapore

    Yu Zhao

Authors
  1. Woon-Yew Siau
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  2. Yao Zhang
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  3. Yu Zhao
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Corresponding author

Correspondence to Yu Zhao .

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Editors and Affiliations

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

    Jianbo Wang

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Siau, WY., Zhang, Y., Zhao, Y. (2012). Stereoselective Synthesis of Z-Alkenes. In: Wang, J. (eds) Stereoselective Alkene Synthesis. Topics in Current Chemistry, vol 327. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2012_315

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