Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates

Journal of the American Chemical Society

Volumn 124, Issue 39, 2002, Pages 11586-11587

  Kennedy, Jason W J ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BORONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0037009989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027453j     Document Type: Article

References (12)

1. (a) Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer-Verlag: Berlin, Heidelberg, 1995; Chapter 7.
2. Roush, W. R. Stereoselective Synthesis, Houben-Weyl, 4th ed.: Thieme: Stuttgart, 1995; Chapter 1.3.3.3.3 in Vol. E21b.
3. Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655-1660.
4. Li, Y.; Houk. K. N. J. Am. Chem. Soc. 1989, 111, 1236-1240.
5. Exceptionally, the related allyltrifluoroborate salts add to aldehydes with high diastereoselectivity using strong Lewis acid catalysts: Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990-998.
6. Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898-899.
7. Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868-1874.
8. Omoto, K.; Fujimoto, H. J. Org. Chem. 1998, 63, 8331-8336.
9. See Supporting Information for details.
10. Hoffmann, R. W.; Schlapbach, A. Tetrahedron 1992, 48, 1959-1968.
11. 3-catalyzed and background uncatalyzed reaction: 3 × for 4, > 35 × for 1a.
12. Zhu, N.; Hall, D. G., unpublished results.