Chiral phosphines in nucleophilic organocatalysis

Yumei Xiao,
Zhanhu Sun,
Hongchao Guo and
Ohyun Kwon

Review
Published 04 Sep 2014

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1. Graphical Abstract
2. Figure 1: Cyclic chiral phosphines based on bridged-ring skeletons.
  
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3. Figure 2: Cyclic chiral phosphines based on binaphthyl skeletons.
  
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4. Figure 3: Cyclic chiral phosphines based on ferrocene skeletons.
  
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5. Figure 4: Cyclic chiral phosphines based on spirocyclic skeletons.
  
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6. Figure 5: Cyclic chiral phosphines based on phospholane ring skeletons.
  
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7. Figure 6: Acyclic chiral phosphines.
  
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8. Figure 7: Multifunctional chiral phosphines based on binaphthyl skeletons.
  
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9. Figure 8: Multifunctional chiral phosphines based on amino acid skeletons.
  
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10. Scheme 1: Asymmetric [3 + 2] annulations of allenoates with electron-deficient olefins, catalyzed by the chir...
  
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11. Scheme 2: Asymmetric [3 + 2] annulations of allenoate and enones, catalyzed by the chiral binaphthyl-based ph...
  
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12. Scheme 3: Asymmetric [3 + 2] annulations of N-substituted olefins and allenoates, catalyzed by the chiral bin...
  
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13. Scheme 4: Asymmetric [3 + 2] annulations of 2-aryl-1,1-dicyanoethylenes with ethyl allenoate, catalyzed by th...
  
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14. Scheme 5: Asymmetric [3 + 2] annulations of 3-alkylideneindolin-2-ones with ethyl allenoate, catalyzed by the...
  
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15. Scheme 6: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the c...
  
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16. Scheme 7: Asymmetric [3 + 2] annulations of allenoate with alkylidene azlactones, catalyzed by the chiral bin...
  
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17. Scheme 8: Asymmetric [3 + 2] annulations of C₆₀ with allenoates, catalyzed by the chiral phosphine B6.
  
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18. Scheme 9: Asymmetric [3 + 2] annulations of α,β-unsaturated esters and ketones with an allenoate, catalyzed b...
  
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19. Scheme 10: Asymmetric [3 + 2] annulations of exocyclic enones with allenoates, catalyzed by the ferrocene-modi...
  
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20. Scheme 11: Asymmetric [3 + 2] annulations of enones with an allenylphosphonate, catalyzed by the ferrocene-mod...
  
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21. Scheme 12: Asymmetric [3 + 2] annulations of 3-alkylidene-oxindoles with ethyl allenoate, catalyzed by the fer...
  
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22. Scheme 13: Asymmetric [3 + 2] annulations of dibenzylideneacetones with ethyl allenoate, catalyzed by the ferr...
  
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23. Scheme 14: Asymmetric [3 + 2] annulations of trisubstituted alkenes with ethyl allenoate, catalyzed by the fer...
  
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24. Scheme 15: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the f...
  
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25. Scheme 16: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with ethyl allenoates, catalyzed by the f...
  
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26. Scheme 17: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with allenoates, catalyzed by the ferrocen...
  
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27. Scheme 18: Asymmetric [3 + 2] annulations of alkylidene azlactones with allenoates, catalyzed by the chiral sp...
  
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28. Scheme 19: Asymmetric [3 + 2] annulations of α-trimethylsilyl allenones and electron-deficient olefins, cataly...
  
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29. Scheme 20: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with an allenone, catalyzed by the chiral...
  
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30. Scheme 21: Asymmetric [3 + 2] annulations of cyclic enones with allenoates, catalyzed by the chiral α-amino ac...
  
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31. Scheme 22: Asymmetric [3 + 2] annulations of arylidenemalononitriles and analogues with an allenoate, catalyze...
  
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32. Scheme 23: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with an allenoate, catalyzed by the chiral...
  
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33. Scheme 24: Asymmetric [3 + 2] annulations of 3,5-dimethyl-1H-pyrazole-derived acrylamides with an allenoate, c...
  
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34. Scheme 25: Asymmetric [3 + 2] annulations of maleimides with allenoates, catalyzed by the chiral phosphine H10....
  
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35. Scheme 26: Asymmetric [3 + 2] annulations of α-substituted acrylates with allenoate, catalyzed by the chiral p...
  
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36. Scheme 27: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
  
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37. Scheme 28: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
  
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38. Scheme 29: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
  
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39. Scheme 30: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with butynoates, catalyzed ...
  
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40. Scheme 31: Asymmetric [3 + 2] annulations of N-tosylimines with allenylphosphonates, catalyzed by the chiral p...
  
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41. Scheme 32: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
  
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42. Scheme 33: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with allenoates (top), cata...
  
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43. Scheme 34: Asymmetric [3 + 2] annulation of N-diphenylphosphinoylimines with allenoates, catalyzed by the chir...
  
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44. Scheme 35: Asymmetric [3 + 2] annulation of an azomethine imine with an allenoate, catalyzed by the chiral pho...
  
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45. Scheme 36: Asymmetric [3 + 2] annulations between α,β-unsaturated esters/ketones and 3-butynoates, catalyzed b...
  
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46. Scheme 37: Asymmetric intramolecular [3 + 2] annulations of electron-deficient alkenes and MBH carbonates, cat...
  
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47. Scheme 38: Asymmetric [3 + 2] annulations of methyleneindolinone and methylenebenzofuranone derivatives with M...
  
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48. Scheme 39: Asymmetric [3 + 2] annulations of activated isatin-based alkenes with MBH carbonates, catalyzed by ...
  
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49. Scheme 40: Asymmetric [3 + 2] annulations of maleimides with MBH carbonates, catalyzed by the chiral phosphine ...
  
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50. Scheme 41: A series of [3 + 2] annulations of various activated alkenes with MBH carbonates, catalyzed by the ...
  
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51. Scheme 42: Asymmetric [3 + 2] annulations of an alkyne with isatins, catalyzed by the chiral phosphine F1.
  
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52. Scheme 43: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine B1.
  
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53. Scheme 44: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H5.
  
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54. Scheme 45: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphines H13 and H12.
  
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55. Scheme 46: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H6.
  
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56. Scheme 47: Kerrigan’s [2 + 2] annulations of ketenes with imines, catalyzed by the chiral phosphine B7.
  
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57. Scheme 48: Asymmetric [4 + 1] annulations, catalyzed by the chiral phosphine G6.
  
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58. Scheme 49: Asymmetric homodimerization of ketenes, catalyzed by the chiral phosphine F5 and F6.
  
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59. Scheme 50: Aza-MBH/Michael reactions, catalyzed by the chiral phosphine G1.
  
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60. Scheme 51: Tandem RC/Michael additions, catalyzed by the chiral phosphine H14.
  
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61. Scheme 52: Intramolecular tandem RC/Michael addition, catalyzed by the chiral phosphine H15.
  
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62. Scheme 53: Double-Michael addition, catalyzed by the chiral aminophosphine G9.
  
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63. Scheme 54: Tandem Michael addition/Wittig olefinations, mediated by the chiral phosphine BIPHEP.
  
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64. Scheme 55: Asymmetric Michael additions, catalyzed by the chiral phosphines H7, H8, and H9.
  
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65. Scheme 56: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphine A1.
  
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66. Scheme 57: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphines E2 and E3.
  
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67. Scheme 58: Intramolecular γ-additions of hydroxy-2-alkynoates, catalyzed by the chiral phosphine D2.
  
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68. Scheme 59: Intra-/intermolecular γ-additions, catalyzed by the chiral phosphine D2.
  
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69. Scheme 60: Intermolecular γ-additions, catalyzed by the chiral phosphines B5 and B3.
  
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70. Scheme 61: Intermolecular γ-additions, catalyzed by the chiral phosphines E6 and B4.
  
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71. Scheme 62: Asymmetric allylic substitution of MBH acetates, catalyzed by the chiral phosphine G2.
  
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72. Scheme 63: Allylic substitutions between MBH acetates or carbonates and an array of nucleophiles, catalyzed by...
  
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73. Scheme 64: Asymmetric acylation of diols, catalyzed by the chiral phosphines E4 and E5.
  
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74. Scheme 65: Kinetic resolution of secondary alcohols, catalyzed by the chiral phosphine E8 and E9.
  
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Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

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Chiral phosphines in nucleophilic organocatalysis

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