Evidence for competing syn and anti pathways in palladium-catalyzed eliminations of acyclic allylic carbonates

Chemistry - A European Journal

Volumn 5, Issue 8, 1999, Pages 2300-2305

  Schwarz, Ido ^a   Braun, Manfred ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Allyl complexes; Eliminations; Olefinations; Palladium; Reaction mechanisms

Indexed keywords

ALKENE; ALLYL COMPOUND; CARBONIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOISOMERISM; THERMODYNAMICS;

EID: 0032839744     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990802)5:8<2300::AID-CHEM2300>3.0.CO;2-T     Document Type: Article

References (30)

1. See: R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 833-863.
2. R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151; Org. React. 1982, 27, 345-390; A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
3. R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151; Org. React. 1982, 27, 345-390; A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
4. R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151; Org. React. 1982, 27, 345-390; A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
5. R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151; Org. React. 1982, 27, 345-390; A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
6. B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303; B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933-7935.
7. B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303; B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933-7935.
8. B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1987, 109, 4753-4755; B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1985, 107, 1781-1783; B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.
9. B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1987, 109, 4753-4755; B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1985, 107, 1781-1783; B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.
10. B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1987, 109, 4753-4755; B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1985, 107, 1781-1783; B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.
11. S. Mecking, L. K. Johnson, L. Wang, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 888-899.
12. B. M. Trost, T. R. Verhoeven, J. M. Fortunak, Tetrahedron Lett. 1979, 2301-2304.
13. J. Tsuji, T. Yamakawa, M. Kaito, T. Mandai, Tetrahedron Lett. 1978, 2075-2078.
14. T. Takahashi, N. Nakagawa, T. Minoshima, H. Yamada, J. Tsuji, Tetrahedron Lett. 1990, 31, 4333-4336.
15. T. Mandai, T. Matsumoto, J. Tsuji, S. Saito, Tetrahedron Lett. 1993, 34, 2513-2516.
16. B. M. Trost, T. R. Verhoeven, J. Am. Chem. Soc. 1978, 100, 3435-3443.
17. a) T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727;
18. b) T. Hayashi, M. Kawatsura, Y. Uozumi, J. Am. Chem. Soc. 1998, 120, 1681-1687.
19. The question of the character of the hydrogen in this type of reaction, i.e., either protic-or hydridelike, has been discussed very recently: B. M. Trost, Chem. Eur. J. 1998, 4, 2405-2412.
20. P. G. Anderson, S. Schab, Organometallics 1995, 14, 1-2.
21. J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956-5957.
22. M. Braun, S. Mroß, I. Schwarz, Synthesis 1998, 83-88.
23. C. H. Heathcock, in Comprehensive Organic Synthesis Vol. 2, (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 181-238.
24. C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn, J. Lampe, J. Org. Chem. 1980, 45, 1066-1081.
25. See: L. Xie, K. M. Isenberger, G. Held, L. M. Dahl, J. Org. Chem. 1997, 62, 7516-7519.
26. The calculation is based on the fact that the eliminations of 6a to 7a/ 7b and 6b to 7a/7b are superposed parallel reactions with complete conversion; see: textbooks of physical chemistry.
27. 4] does not, is assumed to result from the higher reactivity of the former catalyst; see: refs. [8, 9].
28. R. Devant, U. Mahler, M. Braun, Chem. Ber. 1988, 121, 397-406.
29. R. C. Osthoff, S. W. Kantor, Inorg. Synth. 1957, 5, 55-64.
30. A. Klages, Ber. Dtsch. Chem. Ges. 1902, 35, 2245-2262.