On the question of the symmetry of formally symmetrical π-(allyl)palladium cationic intermediates in allylic alkylations

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 235-236

  Trost, Barry M ^a   Bunt, Richard C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000385149     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9530782     Document Type: Article

References (23)

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2. (b) Trost. B. M.; Bunt. R. C J Ain. Chem. Soc. 1994, 116, 4089.
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11. The ee of this reaction with the simple five-membered-ring substrate in contrast to this reaction with other ring sizes is known to be extremely sensitive to temperature. On a larger scale, the internal reaction temperature may not have been rigorously maintained at -78 °C as required for this substrate.
12. Optical rotation data for the acetate (S)-1 was in agreement with the ee determined from the mandelate ester. See: Asami. M. Bull. Chem. Soc. Jpn. 1990. 63. 721.
13. Trost, B. M.; Organ, M. C.; O'Dohery, G. A. J. Am. Chem. Soc. 1995.117,9662.
14. Note that a change in the Cahn-Ingold-Prelog priority rules may in some cases cause the (R) or (S) nomenclature to change irrespective of this retention of configuration.
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16. Akermark, B., Hansson, S.; Krakenberger. B.; Vitaglianano, A.; Zetterberg, K. Organometallics 1984, 3, 679.
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18. Mackenzie. P B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046. See also: Pregosin. P. S.; Salxmann, R.; Togni. A. Organometallics 1994, 15. 842.
19. (a) Yamamoto, K.; Deguchi. R.; Ogimura, Y.; Tsuji, J. Chem. Lett. 1984, 1657.
20. (b) Takahashi. T.; Jinbo. Y.; Kitamura, K.; Tsuji, J. Tetrahedron Lett. 1984, 25. 5921. Note that, for π-allyl's incapable of racemizing via a π-σ-π mechanism, optical activity can be retained in the product, see: Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51. 723.
21. (b) Takahashi. T.; Jinbo. Y.; Kitamura, K.; Tsuji, J. Tetrahedron Lett. 1984, 25. 5921. Note that, for π-allyl's incapable of racemizing via a π-σ-π mechanism, optical activity can be retained in the product, see: Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51. 723.
22. For products where rotation data can now be compared to the Fiaud results, the retained or differential ee's are in the range 5-20%. See Helmchen, G.; Gabler. B.: Sennhenn. P. Tetrahedron Lett. 1994, 35. 8595.
23. For an example, see: von Matt. P.; Lloyd-Jones, G. C.; Minidis. A. B. E.; Pfaltz, A.; Macko. L.; neuberger. M.; Zehnder. M.; Rueggser. H.; Pregosin, P. S. Helv. Chim. Atta 1995, 78. 265.