Bistrifluoromethanesulfonimide in the catalytic conjugate allylation of α,β-unsaturated carbonyl compounds

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3215-3216

  Kuhnert, Nikolai ^a   Peverley, Jonathan ^a   Robertson, Jeremy ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; FLUOROFORM; KETONE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS;

EID: 0032516344     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00394-3     Document Type: Article

References (19)

1. 1. Robertson, J.; Burrows, J. N.; Stupple, P. A. Tetrahedron, 1997, 53, 14807-14820; Robertson, J.; Burrows, J. N. Synthesis, 1998, 63-66.
2. 1. Robertson, J.; Burrows, J. N.; Stupple, P. A. Tetrahedron, 1997, 53, 14807-14820; Robertson, J.; Burrows, J. N. Synthesis, 1998, 63-66.
3. 2. E.g.: Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Am. Chem. Soc., 1990, 112, 4404-4410; Lipshutz, B. H.; Hackmann, C. J. Org. Chem., 1994, 59, 7437-7444
4. 2. E.g.: Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Am. Chem. Soc., 1990, 112, 4404-4410; Lipshutz, B. H.; Hackmann, C. J. Org. Chem., 1994, 59, 7437-7444
5. 3. Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc., 1994, 116, 6130-6141.
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7. 5. Kim, S.; Lee, J. M. Synth. Commun., 1991, 21, 25-29.
8. 6. Mathieu, B.; Ghosez, L. Tetrahedron Lett., 1997, 38, 5497-5500; see also Ishii, A.; Kotera, O.; Saeki, T.; Mikami, K. Synlett, 1997, 1145-1146.
9. 6. Mathieu, B.; Ghosez, L. Tetrahedron Lett., 1997, 38, 5497-5500; see also Ishii, A.; Kotera, O.; Saeki, T.; Mikami, K. Synlett, 1997, 1145-1146.
10. 1H n.m.r. spectroscopy (500 MHz).
11. H (60 MHz) 0.57 (9H, s)}.
12. 2; i.e. the system is self-drying.
13. 2) 1.62 (6H, d, J 6.8), 4.74 (1H, sept, J 6.8).
14. 11. Foropoulos, J., Jr.; DesMarteau, D. D. Inorg. Chem., 1984, 23, 3720-3723.
15. 12. Vij, A.; Zheng, Y. Y.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem., 1994, 33, 3281-3288.
16. 4), and the solvents removed in vacuo. The allylated ketones were obtained as colourless oils after purification by either short-path distillation or column chromatography.
17. 14. A similar sequence has been reported using trityl perchlorate: Hayashi, M.; Mukaiyama, T. Chem. Lett., 1987, 289-292.
18. 15. Jeroncic, L. O.; Cabal, M.-P.; Danishefsky, S. J.; Shulte, G. M. J. Org. Chem., 1991, 56, 387-395.
19. 16. For a discussion see Fleming, I.; Dunoguès, J.; Smithers, R. Org. React., 1989, 37, 57-575.