Results and Discussion

Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

Simple cyclic enones have generally been omitted within the vast majority of studies on the asymmetric epoxidation of α,β-unsaturated ketones. Thus, we decided to focus on these challenging cyclic substrates as a departure point before extending the methodology to different types of α,β-unsaturated ketones.

Keywords

Aldol Reaction Epoxidation Reaction High Enantioselectivity Enantiomeric Ratio Conjugate Addition 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Wang X, List B (2008) Angew Chem Int Ed 47:1119CrossRefGoogle Scholar
  2. 2.
    Martin NJA, List B (2006) J Am Chem Soc 128:13368CrossRefGoogle Scholar
  3. 3.
    Kawara A, Taguchi T (1994) Tetrahedron Lett 35:8805CrossRefGoogle Scholar
  4. 4.
    Yamaguchi M, Shiraishi T, Hirama M (1996) J Org Chem 61:3520CrossRefGoogle Scholar
  5. 5.
    Yamaguchi M, Shiraishi T, Hirama M (1993) Angew Chem Int Ed 32:1176CrossRefGoogle Scholar
  6. 6.
    Hanessian S, Pham V (2000) Org Lett 2:2975CrossRefGoogle Scholar
  7. 7.
    Zhou J, Wakchaure V, Kraft P, List B (2008) Angew Chem Int Ed 47:7656CrossRefGoogle Scholar
  8. 8.
    Mayer S, List B (2006) Angew Chem Int Ed 45:4193CrossRefGoogle Scholar
  9. 9.
    Wynberg H, Marsman B (1980) J Org Chem 45:158CrossRefGoogle Scholar
  10. 10.
    Martin NJA (2008) Ph.D. thesisGoogle Scholar
  11. 11.
    Kienle M, Argyrakis W, Baro A, Laschat S (2008) Tetrahedron Lett 49:1971CrossRefGoogle Scholar
  12. 12.
    Alexakis A, Benhaim C (2002) Eur J Org Chem 2002:3221CrossRefGoogle Scholar
  13. 13.
    Alexakis A, Bäckvall JE, Krause N, Pàmies O, Diéguez M (2008) Chem Rev 108:2796CrossRefGoogle Scholar
  14. 14.
    Stork G, Danheiser RL (1973) J Org Chem 38:1775CrossRefGoogle Scholar
  15. 15.
    Hoke ME, Brescia M-R, Bogaczyk S, DeShong P, King BW, Crimmins MT (2001) J Org Chem 67:327CrossRefGoogle Scholar
  16. 16.
    Baldwin JE, Adlington RM, Mitchell MB (1993) J Chem Soc, Chem Commun (17):1332Google Scholar
  17. 17.
    Sucrow W, Rädecker G (1988) Chem Ber 121:219CrossRefGoogle Scholar
  18. 18.
    Christian CF, Takeya T, Szymanski MJ, Singleton DA (2007) J Org Chem 72:6183CrossRefGoogle Scholar
  19. 19.
    Ramachary DB, Ramakumar K, Kishor M (2005) Tetrahedron Lett 46:7037CrossRefGoogle Scholar
  20. 20.
    Ramachary DB, Ramakumar K, Narayana VV (2008) Chem Eur J 14:9143CrossRefGoogle Scholar
  21. 21.
    Yanagisawa A, Shinohara A, Takahashi H, Arai T (2007) Synlett 1:141CrossRefGoogle Scholar
  22. 22.
    Hong L, Sun W, Liu C, Wang L, Wong K, Wang R (2009) Chem Eur J 15:11105CrossRefGoogle Scholar
  23. 23.
    Yang Y-Q, Zhao G (2008) Chem Eur J 14:10888CrossRefGoogle Scholar
  24. 24.
    Nazarov IN, Akhrem AA (1950) Zh Obshch Khim 20:2183Google Scholar
  25. 25.
    Payne G (1958) J Org Chem 23:310CrossRefGoogle Scholar
  26. 26.
    Fraile JM, García JI, Mayoral JA, Sebti S, Tahirb R (2001) Green Chem 3:271CrossRefGoogle Scholar
  27. 27.
    Cativiela C, Figueras F, Fraile JM, García JI, Mayoral JA (1995) Tetrahedron Lett 36:4125CrossRefGoogle Scholar
  28. 28.
    Paquette LA, Carr RVC, Bellamy F (1978) J Am Chem Soc 100:6764CrossRefGoogle Scholar
  29. 29.
    Rieche A, Schmitz E, Gründemann E (1960) Chem Ber 93:2443CrossRefGoogle Scholar
  30. 30.
    Xie J-W, Chen W, Li R, Zeng M, Du W, Yue L, Chen Y-C, Wu Y, Zhu J, Deng J-G (2007) Angew Chem Int Ed 46:389CrossRefGoogle Scholar
  31. 31.
    Erkkilä A, Pihko PM (2007) Eur J Org Chem 2007:4205CrossRefGoogle Scholar
  32. 32.
    Hamann H-J, Bunge A, Liebscher J (2008) Chem Eur J 14:6849CrossRefGoogle Scholar
  33. 33.
    Carey FA, Sundberg RJ (2007) Advanced organic chemistry. Part A: structure and mechanisms: structure and mechanisms, 5th edn. Springer, New YorkGoogle Scholar
  34. 34.
    Wang X, Reisinger CM, List B (2008) J Am Chem Soc 130:6070CrossRefGoogle Scholar
  35. 35.
    Lu X, Liu Y, Sun B, Cindric B, Deng L (2008) J Am Chem Soc 130:8134CrossRefGoogle Scholar
  36. 36.
    Carlone A, Bartoli G, Bosco M, Pesciaioli F, Ricci P, Sambri L, Melchiorre P (2007) Eur J Org Chem 33:5492CrossRefGoogle Scholar
  37. 37.
    Barnier J-P, Morisson V, Blanco L (2001) Synth Commun 31:349CrossRefGoogle Scholar
  38. 38.
    Kulinkovich OG, Astashko DA, Tyvorskii VI, Ilyina NA (2001) Synthesis 10:1453CrossRefGoogle Scholar
  39. 39.
    Maulide N, Vanherck J-C, Gautier A, Marko IE (2007) Acc Chem Res 40:381CrossRefGoogle Scholar
  40. 40.
    Bailey M, Staton I, Ashton PR, Markó IE, Ollis WD (1991) Tetrahedron: Asymmetry 2:495CrossRefGoogle Scholar
  41. 41.
    Kayser RH, Pollack RM (1975) J Am Chem Soc 97:952CrossRefGoogle Scholar
  42. 42.
    Schuurman RJW, Linden Ad, Grimbergen RPF, Nolte RJM, Scheeren HW (1996) Tetrahedron 52:8307CrossRefGoogle Scholar
  43. 43.
    Aggarwal VK, Mereu A (1999) Chem Commun (22):2311Google Scholar
  44. 44.
    Bartoli G, Bosco M, Carlone A, Pesciaioli F, Sambri L, Melchiorre P (2007) Org Lett 9:1403CrossRefGoogle Scholar
  45. 45.
    Xie J-W, Huang X, Fan L-P, Xu D-C, Li X-S, Su H, Wen Y-H (2009) Adv Synth Catal 351:3077CrossRefGoogle Scholar
  46. 46.
    Fehr C, Galindo J (2005) Helv Chim Acta 88:3128CrossRefGoogle Scholar
  47. 47.
    Dussault PH, Liu X (1999) Org Lett 1:1391CrossRefGoogle Scholar
  48. 48.
    Kirihara M, Kakuda H, Ichinose M, Ochiai Y, Takizawa S, Mokuya A, Okubo K, Hatano A, Shiro M (2005) Tetrahedron 61:4831CrossRefGoogle Scholar
  49. 49.
    Chung WK, Lam SK, Lo B, Liu LL, Wong W-T, Chiu P (2009) J Am Chem Soc 131:4556CrossRefGoogle Scholar
  50. 50.
    Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471CrossRefGoogle Scholar
  51. 51.
    Machajewski TD, Wong C-H (2000) Angew Chem Int Ed 39:1352CrossRefGoogle Scholar
  52. 52.
    Geary LM, Hultin PG (2009) Tetrahedron: Asymmetry 20:131CrossRefGoogle Scholar
  53. 53.
    Mahrwald RE (ed) (2004) Modern aldol reactions. Wiley-VCH, WeinheimGoogle Scholar
  54. 54.
    Guillena G, Nájera C, Ramón DJ (2007) Tetrahedron: Asymmetry 18:2249CrossRefGoogle Scholar
  55. 55.
    Krattiger P, Kovasy R, Revell JD, Ivan S, Wennemers H (2005) Org Lett 7:1101CrossRefGoogle Scholar
  56. 56.
    Tang Z, Jiang F, Cui X, Gong L-Z, Mi A-Q, Jiang Y-Z, Wu Y-D (2004) Proc Natl Acad Sci USA 101:5755CrossRefGoogle Scholar
  57. 57.
    Tang Z, Jiang F, Yu L-T, Cui X, Gong L-Z, Mi A-Q, Jiang Y-Z, Wu Y-D (2003) J Am Chem Soc 125:5262CrossRefGoogle Scholar
  58. 58.
    List B, Pojarliev P, Castello C (2001) Org Lett 3:573CrossRefGoogle Scholar
  59. 59.
    Morisson V, Barnier J-P, Blanco L (1999) Tetrahedron Lett 40:4045CrossRefGoogle Scholar
  60. 60.
    Griesbaum K, Kim WS (1992) J Org Chem 57:5574CrossRefGoogle Scholar
  61. 61.
    Baumstark AL, Vasquez PC, Chen Y (1993) Heteroat Chem 4:175CrossRefGoogle Scholar
  62. 62.
    Makarov SV (2001) Russ Chem Rev 70:885CrossRefGoogle Scholar
  63. 63.
    Li DR, Murugan A, Falck JR (2007) J Am Chem Soc 130:46CrossRefGoogle Scholar
  64. 64.
    Körber K, Risch P, Brückner R (2005) Synlett 19:2905Google Scholar
  65. 65.
    Corey EJ, Ensley HE (1973) J Org Chem 38:3187CrossRefGoogle Scholar
  66. 66.
    Molander GA, Hahn G (1986) J Org Chem 51:2596CrossRefGoogle Scholar
  67. 67.
    Miyashita M, Suzuki T, Yoshikoshi A (1987) Tetrahedron Lett 28:4293CrossRefGoogle Scholar
  68. 68.
    Engman L, Stern D (2002) J Org Chem 59:5179CrossRefGoogle Scholar
  69. 69.
    Jung ME, Allen DA (2008) Org Lett 10:2039CrossRefGoogle Scholar
  70. 70.
    Miyashita M, Suzuki T, Hoshino M, Yoshikoshi A (1997) Tetrahedron 53:12469CrossRefGoogle Scholar
  71. 71.
    Pidathala C, Hoang L, Vignola N, List B (2003) Angew Chem Int Ed 42:2785CrossRefGoogle Scholar
  72. 72.
    Ghobril C, Sabot C, Mioskowski C, Baati R (2008) Eur J Org Chem (24):4104Google Scholar
  73. 73.
    McCullough KJ, Nojimab M (2001) Curr Org Synth 5:601Google Scholar
  74. 74.
    Dussault PH, Zope U (1995) Tetrahedron Lett 36:3655CrossRefGoogle Scholar
  75. 75.
    Tokuyasu T, Ito T, Masuyama A, Nojima M (2000) Heterocycles 53:1293CrossRefGoogle Scholar
  76. 76.
    Dussault PH, Lee RJ, Schultz JA, Suh YS (2000) Tetrahedron Lett 41:5457CrossRefGoogle Scholar
  77. 77.
    Dussault PH, Lee IQ, Lee H-J, Lee RJ, Niu QJ, Schultz JA, Zope UR (2000) J Org Chem 65:8407CrossRefGoogle Scholar
  78. 78.
    Dussault PH, Trullinger TK, Cho-Shultz S (2000) Tetrahedron 56:9213CrossRefGoogle Scholar
  79. 79.
    Courtneidge JL, Bush M, Loh LS (1992) Tetrahedron 48:3835CrossRefGoogle Scholar
  80. 80.
    Baba N, Oda J, Kawahara S, Hamada M (1989) Bull Inst Chem Res Kyoto Univ 67:121Google Scholar
  81. 81.
    Zajac WW, Walters TR, Darcy MG (1988) J Org Chem 53:5856CrossRefGoogle Scholar
  82. 82.
    Baidya M, Horn M, Zipse H, Mayr H (2009) J Org Chem 74:7157CrossRefGoogle Scholar
  83. 83.
    Aggarwal VK, Lopin C, Sandrinelli F (2003) J Am Chem Soc 125:7596CrossRefGoogle Scholar
  84. 84.
    Chen W, Du W, Duan Y-Z, Wu Y, Yang S-Y, Chen Y-C (2007) Angew Chem Int Ed 46:7667CrossRefGoogle Scholar
  85. 85.
    Kelly DR, Caroff E, Flood RW, Heal W, Roberts SM (2004) Chem Commun 2016Google Scholar
  86. 86.
    Kelly DR, Roberts SM (2006) Pept Sci 84:74CrossRefGoogle Scholar
  87. 87.
    Woods GF, Tucker IW (1948) J Am Chem Soc 70:2174CrossRefGoogle Scholar
  88. 88.
    Woods GF, Griswold PH, Armbrecht BH, Blumenthal DI, Plapinger R (1949) J Am Chem Soc 71:2028CrossRefGoogle Scholar
  89. 89.
    Ito Y, Hirao T, Saegusa T (1978) J Org Chem 43:1011CrossRefGoogle Scholar
  90. 90.
    Hadjiarapoglou L, Klein I, Spitzner D, de Meijere A (1996) Synthesis 525Google Scholar
  91. 91.
    Yu J-Q, Corey EJ (2002) Org Lett 4:2727CrossRefGoogle Scholar
  92. 92.
    Larock RC, Hightower TR, Kraus GA, Hahn P, Zheng D (1995) Tetrahedron Lett 36:2423CrossRefGoogle Scholar
  93. 93.
    Cahiez G, Avedissian H (1998) Synthesis 1199Google Scholar
  94. 94.
    Trnka TM, Grubbs RH (2000) Acc Chem Res 34:18CrossRefGoogle Scholar
  95. 95.
    Chatterjee AK, Morgan JP, Scholl M, Grubbs RH (2000) J Am Chem Soc 122:3783CrossRefGoogle Scholar
  96. 96.
    Tietze LF, Henrich M, Niklaus A, Buback M (1999) Chem Eur J 5:297CrossRefGoogle Scholar
  97. 97.
    Oare DA, Henderson MA, Sanner MA, Heathcock CH (1990) J Org Chem 55:132CrossRefGoogle Scholar
  98. 98.
    Usuda H, Kuramochi A, Kanai M, Shibasaki M (2004) Org Lett 6:4387CrossRefGoogle Scholar
  99. 99.
    Brunner H, Bügler J, Nuber B (1995) Tetrahedron: Asymmetry 6:1699CrossRefGoogle Scholar
  100. 100.
    Brunner H, Bügler J (1997) Bull Soc Chim Belg 106:77Google Scholar
  101. 101.
    Brunner H, Schmidt P (2000) Eur J Org Chem (11):2119Google Scholar
  102. 102.
    Zhang E, Fan C-A, Tu Y-Q, Zhang F-M, Song Y-L (2009) J Am Chem Soc 131:14626CrossRefGoogle Scholar
  103. 103.
    McCooey SH, Connon SJ (2007) Org Lett 9:599CrossRefGoogle Scholar
  104. 104.
    Vakulya B, Varga S, Csámpai A, Soós T (2005) Org Lett 7:1967CrossRefGoogle Scholar
  105. 105.
    Berkessel A, Guixá M, Schmidt F, Neudörfl JM, Lex J (2007) Chem Eur J 13:4483CrossRefGoogle Scholar
  106. 106.
    Franz MH, Röper S, Wartchow R, Hoffmann HMR (2004) J Org Chem 69:2983CrossRefGoogle Scholar
  107. 107.
    Kessar SV, Singh P, Singh KN, Singh SK (1999) Chem Commun (19):1927Google Scholar
  108. 108.
    Kessar SV, Singh P, Vohra R, Kaur NP, Singh KN (1991) J Chem Soc, Chem Commun (8):568Google Scholar
  109. 109.
    Kessar SV, Singh P, Kaur A, Singh S (2003) ARKIVOC 3:120Google Scholar
  110. 110.
    Li J, Luo S, Cheng J-P (2009) J Org Chem 74:1747CrossRefGoogle Scholar
  111. 111.
    Simonsen KB, Gothelf KV, Jorgensen KA (1998) J Org Chem 63:7536CrossRefGoogle Scholar
  112. 112.
    Wipf P, Jung J-K (2000) J Org Chem 65:6319CrossRefGoogle Scholar
  113. 113.
    Zhu SS, Cefalo DR, La DS, Jamieson JY, Davis WM, Hoveyda AH, Schrock RR (1999) J Am Chem Soc 121:8251CrossRefGoogle Scholar
  114. 114.
    Seayad J, Seayad AM, List B (2006) J Am Chem Soc 128:1086CrossRefGoogle Scholar
  115. 115.
    Akiyama T (2004) WO2004096753, PCT Int ApplGoogle Scholar
  116. 116.
    Storer RI, Carrera DE, Ni Y, MacMillan DWC (2005) J Am Chem Soc 128:84CrossRefGoogle Scholar
  117. 117.
    Maruoka K, Itoh T, Araki Y, Shirasaka T, Yamamoto H (1988) Bull Chem Soc Jpn 61:2975CrossRefGoogle Scholar

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© Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  1. 1.Max-Planck-Institut für KohlenforschungMülheim an der RuhrGermany

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