Palladium-catalyzed enantioselective conjugate addition of arylboronic acids

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5309-5312

  Gini, Francesca ^a   Hessen, Bart ^a   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244489932     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052222d     Document Type: Article

References (48)

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9. The enantioselective addition of diphenylzinc and phenylmagnesium bromide to 2-cyclohexenone has also been achieved; see: (d) Peña, D.; López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1636.
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24. For a comprehensive overview of palladium chemistry, see: (b) Handbook of Organopalladium Chemistry for Organic synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
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28. (b) For the coupling of arylboronic acids to alkynes, see: Zhou, C.; Larock, R. C. Org. Lett. 2005, 7, 259 and references therein.
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31. It should be noted that the palladium(II)-catalyzed addition of arylboronic acids to bicyclic alkenes has been reported; see: Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695. The asymmetric version using Tol-BINAP afforded ee's up to 71%.
32. Albéniz, A. C.; Catalina, N. M.; Espinet, P.; Redón, R. Organometallics 1999, 18, 5571.
33. The oxidative Heck-arylation using arylboronic acids and Pd/ phenanthroline complexes has recently been reported, see: (a) Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218.
34. (b) Andappan, M. M. S.; Nilsson, P.; Von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212.
35. Although all reactions were performed in THF/water 10:1 as solvent, reactions can be performed as well in pure THF. Reaction rates are somewhat decreased but ee's are unaffected.
36. See ref 20a: in that study, boronic acids with electronwithdrawing groups at the meta position gave only moderate yield and para substituents refused to react.
37. Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240.
38. (a) Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850.
39. For examples using achiral catalysts, see: (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450.
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41. 2-catalyzed addition of triphenylbismuth to 2-hexenal afforded the conjugate addition product in 55% yield, 68% ee; see ref 16.
42. 1H NMR analysis. The enantioselectivity of 3o in the mixture was determined by chiral GC. Compound 4 was synthesized for comparison according to a literature procedure (See Supporting Information).
43. (a) Reference 15a. The rhodium-catalyzed enantioselective addition of arylboronic acids to substituted cinnamic esters has recently been reported;
44. see: (b) Paquin, J.-F.; Stephenson, C. R. J.; Defieber, C.; Carreira, E. M. Org. Lett. 2005, 7, 3821.
45. The rhodium-catalyzed enantioselective addition to aliphatic esters has been reported in: (c) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
46. (d) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
47. (e) Navarre, L.; Pucheault, M.; Darses, S.; Genet, J.-P. Tetrahedron Lett. 2005, 46, 4247.
48. Substrate 1i has been used successfully in the corresponding rhodium-catalyzed reaction; see: Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719 and references therein.