Chloride effect on the palladium-catalyzed allylic substitution vs elimination of cyclic vinyloxazolidinones and oxazolines

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 4991-4994

  Cook, Gregory R ^a   Shanker, P Sathya ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032499973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00976-9     Document Type: Article

References (16)

1. 1. For recent reviews, see: (a) Hegedus, L. in Organometallics in Synthesis; Schlösser, M., Ed.; J. Wiley: New York, 1994; pp 385-459.
2. (b) Palladium Reagents and Catalysis; Tsuji, J.; Ed.; Wiley: New York, 1995.
3. (c) Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395.
4. (d) Guibé, F. Tetrahedron 1998, 54, 2967.
5. 2. (a) Tsuji, J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 2075.
6. (b) Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 2301.
7. 3. For a recent report of iodide influencing the regioselectivity in a Pd-catalyzed allylic alkylation, see: Kawatsura, M.; Uozumi, Y.; Hayashi, T. Chem. Comm. 1998, 217.
8. 4. The addition of LiCl to π-allyl palladium intermediates has been known to alter the stereochemistry of acetate addition via displacement of acetate from the Pd. (a) Bäckvall, S. E.; Nordberg, R. E. J. Am. Chem. Soc. 1981, 103, 4959.
9. (b) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
10. 5. An anion effect on enantioselectivity in the Pd-catalyzed allylic amination has been reported. Burckhardt, U.; Maumann, M.; Togni, A. Tetrahedron Asymm. 1997, 8, 155.
11. 4NCl also inhibited elimination reactions. Keinan E.; Roth, Z. Israel J. Chem. 1990, 30, 305.
12. 7. Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 3405.
13. 1H NMR (400 MHz).
14. 9. For mechanistic evidence of the general base-promoted elimination of π-allyl palladium intermediates, see: (a) Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1.
15. (b) Takacs, J. M.; Lawson, E. C.; Clement, F. J. Am. Chem. Soc. 1997, 119, 5956.
16. 2 was. See ref 2a.